2-Oxo-2-phenylacetic acid (Phenylglyoxylic Acid)

Page 1

Reactions (3319)

Yield

Substances (4702)

Citations (815)

Conditions

References

199

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Rx-ID: 29691248

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90%

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With dipotassium peroxodisulfate; bis(benzonitrile)palladium(II) dichloride; silver(l) oxide in 1,4-dioxane; acetic acid; dimethyl sulfoxide

T=120°C; 12 h;

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Li, Mingzong; Ge, Haibo

Organic Letters, 2010 , vol. 12, # 15 p. 3464 - 3467 Title/Abstract Full Text View citing articles Show Details

200

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Rx-ID: 29691250

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95%

With dipotassium peroxodisulfate; bis(benzonitrile)palladium(II) dichloride; silver(l) oxide in 1,4-dioxane; acetic acid; dimethyl sulfoxide

T=120°C; 12 h;

Li, Mingzong; Ge, Haibo

Organic Letters, 2010 , vol. 12, # 15 p. 3464 - 3467 Title/Abstract Full Text View citing articles Show Details

201

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Rx-ID: 29691252

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85%

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With dipotassium peroxodisulfate; bis(benzonitrile)palladium(II) dichloride; silver(l) oxide in 1,4-dioxane; acetic acid; dimethyl sulfoxide

T=120°C; 12 h;

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Li, Mingzong; Ge, Haibo

Organic Letters, 2010 , vol. 12, # 15 p. 3464 - 3467 Title/Abstract Full Text View citing articles Show Details

202

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Rx-ID: 29691257

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93%

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With dipotassium peroxodisulfate; bis(benzonitrile)palladium(II) dichloride; silver(l) oxide in 1,4-dioxane; acetic acid; dimethyl sulfoxide

T=120°C; 12 h;

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Li, Mingzong; Ge, Haibo

Organic Letters, 2010 , vol. 12, # 15 p. 3464 - 3467 Title/Abstract Full Text View citing articles Show Details

203

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90%

With ammonium peroxydisulfate; palladium(II) trifluoroacetate in diethylene glycol dimethyl ether

T=20°C;

Fang, Ping; Li, Mingzong; Ge, Haibo

Journal of the American Chemical Society, 2010 , vol. 132, # 34 p. 11898 - 11899 Title/Abstract Full Text View citing articles Show Details

74%

With oxygen; palladium diacetate; eosin y in chlorobenzene

T=20°C; 15 h; Irradiation;

Zhou, Chao; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Organic Letters, 2015 , vol. 17, # 24 p. 6198 - 6201 Title/Abstract Full Text View citing articles Show Details

204

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Rx-ID: 30786415

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98%

With dipotassium peroxodisulfate; palladium diacetate in water; dimethyl sulfoxide

T=20°C; 3 h;

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Li, Mingzong; Wang, Cong; Ge, Haibo

Organic Letters, 2011 , vol. 13, # 8 p. 2062 - 2064 Title/Abstract Full Text View citing articles Show Details

205

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Rx-ID: 30786432

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90%

206

With dipotassium peroxodisulfate; palladium diacetate in water; dimethyl sulfoxide

T=20°C; 3 h;

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Li, Mingzong; Wang, Cong; Ge, Haibo

Organic Letters, 2011 , vol. 13, # 8 p. 2062 - 2064 Title/Abstract Full Text View citing articles Show Details


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Rx-ID: 30786434

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95%

With dipotassium peroxodisulfate; palladium diacetate in water; dimethyl sulfoxide

T=20°C; 3 h;

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Li, Mingzong; Wang, Cong; Ge, Haibo

Organic Letters, 2011 , vol. 13, # 8 p. 2062 - 2064 Title/Abstract Full Text View citing articles Show Details

207

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Rx-ID: 30786437

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98%

With dipotassium peroxodisulfate; palladium diacetate in water; dimethyl sulfoxide

T=20°C; 3 h;

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Li, Mingzong; Wang, Cong; Ge, Haibo

Organic Letters, 2011 , vol. 13, # 8 p. 2062 - 2064 Title/Abstract Full Text View citing articles Show Details

208

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Rx-ID: 30786439

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90%

With dipotassium peroxodisulfate; palladium diacetate in water; dimethyl sulfoxide

T=20°C; 3 h;

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Li, Mingzong; Wang, Cong; Ge, Haibo

Organic Letters, 2011 , vol. 13, # 8 p. 2062 - 2064 Title/Abstract Full Text View citing articles Show Details


209

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Rx-ID: 30951165

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85%

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Yin, Handong; Li, Jing; Hong, Min; Cui, Jichun; Dong, Lei; Zhang, Qijun

Journal of Molecular Structure, 2011 , vol. 985, # 2-3 p. 261 - 269 Title/Abstract Full Text View citing articles Show Details

in methanol

4 h; Reflux; Hide Experimental Procedure

2.2. Synthesis of Schiff base ligand-phenylglyoxylic acid isonicotinyl hydrazone

In typical procedure, isonicotinyl hydrazide (1.37 g, 10 mmol) and phenylglyoxylic acid (1.80 g, 10 mmol) was added in CH3OH (60 ml). The mixture was mechanically stirred and reflux for 4 h. After evaporation of the solvent, the crude product was collected, it was washed first with ethanol and then with dichloromethane-ethanol. For some time, yellow single crystal was formed. Yield: 85percent

210

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Rx-ID: 34021557

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89%

With Fe(III)(edta); dihydrogen peroxide; palladium diacetate; sodium hydroxide in water

T=20°C; pH=7.2 - 7.8; 0.2 h;

Sharma, Sugandha; Khan, Imran A.; Saxena, Anil K.

Advanced Synthesis and Catalysis, 2013 , vol. 355, # 4 p. 673 - 678 Title/Abstract Full Text View citing articles Show Details

73%

With dipotassium peroxodisulfate; palladium diacetate; silver(l) oxide in dimethyl sulfoxide; N,N-dimethyl-formamide

T=20°C; Inert atmosphere;

Wang, Hua; Guo, Li-Na; Duan, Xin-Hua

Organic Letters, 2012 , vol. 14, # 17 p. 4358 - 4361 Title/Abstract Full Text View citing articles Show Details

211

Rx-ID: 34021570

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85%

With Fe(III)(edta); dihydrogen peroxide; palladium diacetate; sodium hydroxide in water

T=20°C; pH=7.2 - 7.8; 0.366667 h;

Sharma, Sugandha; Khan, Imran A.; Saxena, Anil K.

Advanced Synthesis and Catalysis, 2013 , vol. 355, # 4 p. 673 - 678 Title/Abstract Full Text View citing articles Show Details

66%

With dipotassium peroxodisulfate; palladium diacetate; silver(l) oxide in dimethyl sulfoxide; N,N-dimethyl-formamide

T=20°C; Inert atmosphere;

Wang, Hua; Guo, Li-Na; Duan, Xin-Hua

Organic Letters, 2012 , vol. 14, # 17 p. 4358 - 4361 Title/Abstract Full Text View citing articles Show Details

212

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Rx-ID: 36099317

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74%

With diethylamino-sulfur trifluoride; triethylamine in dichloromethane

T=20°C; 16 h; Inert atmosphere;

Vandamme, Mathilde; Bouchard, Léa; Gilbert, Audrey; Keita, Massaba; Paquin, Jean-François

Organic Letters, 2016 , vol. 18, # 24 p. 6468 - 6471 Title/Abstract Full Text Show Details

With sulfuric acid in cyclohexane

3 h; Reflux;

Takizawa, Shinobu; Remond, Emmanuelle; Arteaga, Fernando Arteaga; Yoshida, Yasushi; Sridharan, Vellaisamy; Bayardon, Jerome; Juge, Sylvain; Sasai, Hiroaki

Chemical Communications, 2013 , vol. 49, # 75 p. 8392 - 8394 Title/Abstract Full Text View citing articles Show Details

A

B

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213

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With dipotassium peroxodisulfate; silver nitrate in water; dimethyl sulfoxide

T=20°C; 24 h; Inert atmosphereSchlenk techniqueSealed tube; Overall yield = 35 percent; regioselective reaction; Hide Experimental Procedure

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Wang, Hua; Zhou, Shi-Liu; Guo, Li-Na; Duan, Xin-Hua

Tetrahedron, 2015 , vol. 71, # 4 p. 630 - 636 Title/Abstract Full Text View citing articles Show Details

1:4.3. General procedure for the decarboxylative acylation of coumarins with α-oxocarboxylic acids

General procedure: A 10mL oven-dried Schlenk-tube was charged with AgNO3 (3.4mg, 10molpercent), coumarin (1, 0.2mmol, 1.0equiv), and K2S2O8 (108mg, 0.4mmol, 2.0equiv). The tube was evacuated and backfilled with nitrogen (three times). α-Oxocarboxylic acids (2, 0.48mmol, 2.4equiv) in DMSO/H2O (1:1) 2mL were added by syringe. The tube was then sealed and the mixture was stirred for 24h at room temperature. Upon completion of the reaction, the mixture was diluted with EtOAc, filtered through a pad of Celite, and the filtrate was then removed under vacuo. The residue was purified with chromatography column on silica gel (gradient eluent of EtOAc/petroleum ether: 1:30 to 1:15) to give the corresponding products 3 or 4 in yields listed in Tables 2 and 3.


214

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Rx-ID: 41079814

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91%

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With dipotassium hydrogenphosphate; C36H18F10IrN4(1+)*F6P(1) in dichloromethane; water

T=20°C; 9 h; Schlenk techniqueIrradiation;

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Wang, Guang-Zu; Shang, Rui; Cheng, Wan-Min; Fu, Yao

Organic Letters, 2015 , vol. 17, # 19 p. 4830 - 4833 Title/Abstract Full Text View citing articles Show Details

215

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Rx-ID: 41079815

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94%

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With dipotassium hydrogenphosphate; C36H18F10IrN4(1+)*F6P(1) in dichloromethane; water

T=20°C; 9 h; Schlenk techniqueIrradiation;

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Wang, Guang-Zu; Shang, Rui; Cheng, Wan-Min; Fu, Yao

Organic Letters, 2015 , vol. 17, # 19 p. 4830 - 4833 Title/Abstract Full Text View citing articles Show Details

216

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Rx-ID: 41079816

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88%

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With dipotassium hydrogenphosphate; C36H18F10IrN4(1+)*F6P(1) in dichloromethane; water

T=20°C; 9 h; Schlenk techniqueIrradiation;

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Wang, Guang-Zu; Shang, Rui; Cheng, Wan-Min; Fu, Yao

Organic Letters, 2015 , vol. 17, # 19 p. 4830 - 4833 Title/Abstract Full Text View citing articles Show Details


217

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Rx-ID: 41079819

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89%

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With dipotassium hydrogenphosphate; C36H18F10IrN4(1+)*F6P(1) in dichloromethane; water

T=20°C; 9 h; Schlenk techniqueIrradiation; Reagent/catalystConcentrationSolvent;

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Wang, Guang-Zu; Shang, Rui; Cheng, Wan-Min; Fu, Yao

Organic Letters, 2015 , vol. 17, # 19 p. 4830 - 4833 Title/Abstract Full Text View citing articles Show Details

218

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Rx-ID: 41975318

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87%

With ammonium peroxydisulfate; palladium diacetate in diethylene glycol dimethyl ether

T=20°C; 18 h; Sealed tube;

Wu, Yinuo; Sun, Lei; Chen, Yunyun; Zhou, Qian; Huang, Jia-Wu; Miao, Hui; Luo, Hai-Bin

Journal of Organic Chemistry, 2016 , vol. 81, # 3 p. 1244 - 1250 Title/Abstract Full Text View citing articles Show Details

78%

With dipotassium peroxodisulfate; palladium(II) trifluoroacetate in diethylene glycol dimethyl ether

T=80°C; 20 h; Inert atmosphere; Catalytic behavior; regioselective reaction; Hide Experimental Procedure

Zhang, Liang; Wang, Zhe; Guo, Peiyu; Sun, Wei; Li, Ya-Min; Sun, Meng; Hua, Chengwen

Tetrahedron Letters, 2016 , vol. 57, # 23 p. 2511 - 2514 Title/Abstract Full Text View citing articles Show Details

General catalytic procedure forortho-acylation of N-nitrosoaniline with α-keto acids.

General procedure: An oven-dried 10 mL screw-capped vial was charged with Pd(TFA)2 (6.6 mg, 0.02 mmol, 10 mol percent), N-methyl-N-nitrosoaniline (27.2 mg, 0.2 mmol, 1.0 equiv),α-oxocarboxylic acids (60.0 mg, 0.4 mmol, 2.0 equiv) and K2S2O8 (108.1 mg, 0.4 mmol, 2.0 equiv) under a gentle stream of argon. After Diglyme (1 mL) was added to the vial by a syringe. The vessel was heated in an oil bath at 80 °C for 20 h followed by cooling. The contents were subjected to flash chromatography to give the corresponding product (89percent) as a pale yellow oil. The purified material was dried under an oil-pump vacuum.

219


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Rx-ID: 43006151

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72%

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Yan, Yan-Mei; Gao, Yun; Ding, Ming-Wu

Tetrahedron, 2016 , vol. 72, # 35 p. 5548 - 5557 Title/Abstract Full Text View citing articles Show Details

in methanol

T=20°C; Ugi Condensation; Hide Experimental Procedure

4.4. Synthesis of azides 10 via Ugi reaction

General procedure: Benzaldehyde 3 (R2Ph,0.212 g, 2 mmol), 2-oxopropanoic acid 9 (R3Me, 0.176 g, 2 mmol),and t-butylisocyanide 5 (R4t-Bu, 0.166 g, 2 mmol) were addedsequentially to a solution of 2-azidobenzenamine 2 (R1H, 0.268 g,2 mmol) in methanol (15 mL) at room temperature. The reactionmixture was stirred at ambient temperature for 24e48 h. After thesolvent was evaporated, the crude reaction mixture was purified bycolumn chromatography with EtOAc/petroleum (1:5) as the eluentto give azide 10a.

220

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Rx-ID: 43055690

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71%

With water; oxygen in 1,4-dioxane

T=20°C; 48 h; Schlenk techniqueIrradiation;

Xu, Wen-Tao; Huang, Bei; Dai, Jian-Jun; Xu, Jun; Xu, Hua-Jian

Organic Letters, 2016 , vol. 18, # 13 p. 3114 - 3117 Title/Abstract Full Text View citing articles Show Details

50%

With silver trifluoromethanesulfonate in water; acetonitrile

T=60°C; 24 h; Schlenk technique;

Xu, Xiao-Lan; Xu, Wen-Tao; Wu, Ji-Wei; He, Jian-Bo; Xu, Hua-Jian

Organic and Biomolecular Chemistry, 2016 , vol. 14, # 42 p. 9970 - 9973 Title/Abstract Full Text Show Details

221

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Rx-ID: 43529783

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95%

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With potassium pyrosulfate; palladium dichloride in 1,2dichloro-ethane

T=80°C; 24 h; Reagent/catalystTemperature; regioselective reaction;

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Chen, Xiaopei; Cui, Xiuling; Wu, Yangjie

Organic Letters, 2016 , vol. 18, # 15 p. 3722 - 3725 Title/Abstract Full Text View citing articles Show Details


222

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Rx-ID: 43529797

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90%

With potassium pyrosulfate; palladium dichloride in 1,2dichloro-ethane

T=80°C; 24 h; regioselective reaction;

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Chen, Xiaopei; Cui, Xiuling; Wu, Yangjie

Organic Letters, 2016 , vol. 18, # 15 p. 3722 - 3725 Title/Abstract Full Text View citing articles Show Details

223

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Rx-ID: 728434

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70%

With sulfuric acid; nitric acid

With nitric acid

T=-10°C;

Reich; Morel

Bulletin de la Societe Chimique de France, 1917 , vol. <4> 21, p. 226 Full Text Show Details

With sulfuric acid; potassium nitrate

T=0 - 25°C; 3 h; Hide Experimental Procedure

SHANGHAI FOCHON PHARMACEUTICAL CO LTD; WANG, Weibo; ZHAO, Xingdong; YUAN, Quan; SHI, Hailong; TIAN, Qiang; LIU, Qihong; ZHOU, Zuwen; WANG, Xianlong; CHEN, Zhifang; CHEN, Ling; TAN, Haohan; FANG, Bo; JIANG, Lihua; LIU, Yanxin; SUN, Jing; ZENG, Fanxin; LI, Tongshuang

Patent: WO2014/169843 A1, 2014 ; Location in patent: Page/Page column 48 ;

Chiou, Yu-Min; Que Jr., Lawrence

Journal of the American Chemical Society, 1995 , vol. 117, # 14 p. 3999 - 4013 Title/Abstract Full Text View citing articles Show Details

Title/Abstract Full Text Show Details

2- (3-nitrophenyl)-2-oxoacetic acid (A-1)

To a solution of 2-oxo-2-phenylacetic acid (50.0 g, 0.33 mol) in H2S04 (400 mL) was addedKNOB (40.4 g, 0.4 mol) at 0 °C. The mixture was warmed to ambient temperature and stirred at25 °C for 3 h. The reaction mixture was poured into ice-water (1.6 L) and extracted with EtOAc(2 x 300 mL). The organic extracts were combined and washed with water, brine and dried overanhydrous sodium sulfate and concentrated in vacuo to give the title compound A-i as crudeproduct (63.1 g, 97percent).

224


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Rx-ID: 728443

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80%

With formaldehyd; palladium dichloride in sodium hydroxide

T=65°C; Hydrogenation;

Arterburn; Pannala; Gonzalez; Chamberlin

Tetrahedron Letters, 2000 , vol. 41, # 41 p. 7847 - 7849 Title/Abstract Full Text View citing articles Show Details

37%

With dimethyl viologen in water

T=25°C; 3 h; var. additive; Product distribution;

Park, Joon Woo

Tetrahedron Letters, 1995 , vol. 36, # 15 p. 2637 - 2638 Title/Abstract Full Text View citing articles Show Details

With sodium amalgam; water

racemic mandelic acid;

Claisen

Chemische Berichte, 1877 , vol. 10, p. 847 Full Text Show Details

Hide Details

225

With palladium; dimethyl amine

T=10 - 15°C; Hydrogenation;

Knoop; Oesterlin

Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1925 , vol. 148, p. 311 Hoppe-Seyler's Zeitschrift fuer Physiologische Chemie, 1927 , vol. 170, p. 187,195 Full Text Show Details

With hydrogenchloride; amalgamated zinc

T=90 - 100°C;

Steinkopf; Wolfram

Justus Liebigs Annalen der Chemie, 1923 , vol. 430, p. 159 Full Text Show Details

5.5E-6 mol

With phosphate buffer; ADH (EC 1.1.1.2); MV2+; nicotinamide adenine dinucleotide phosphate in water; tert-butyl alcohol

30 h; electrolysis; other reaction system;

Yuan, Ruo; Watanabe, Shozo; Kuwabata, Susumu; Yoneyama, Hiroshi

Journal of Organic Chemistry, 1997 , vol. 62, # 8 p. 2494 - 2499 Title/Abstract Full Text View citing articles Show Details

With fructose 1,6-biphosphate; Bacillus stearothermophilus; triethanolamine hydrochloride; Reduced nicotinamide-adenine dinucleotide

T=25°C; also in presence of Gln102 or Asn enzyme; Rate constantEquilibrium constant;

Luyten, Marcel A.; Bur, Daniel; Wynn, Hla; Parris, Wendy; Glod, Marvin; et al.

Journal of the American Chemical Society, 1989 , vol. 111, # 17 p. 6800 - 6804 Title/Abstract Full Text View citing articles Show Details

With triethanolamine; isopropyl alcohol; [Ru(bpy)2](PF6)2 Meerwein-Ponndorf-Verley reduction; Irradiation;

Herance, Jose Raul; Ferrer, Belen; Bourdelande, Jose Luis; Marquet, Jordi; Garcia, Hermenegildo

Chemistry - A European Journal, 2006 , vol. 12, # 14 p. 3890 - 3895 Title/Abstract Full Text View citing articles Show Details


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Rx-ID: 1318562

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77%

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With ammonium perchlorate; oxygen; N-ethyl-N,Ndiisopropylamine; trifluoroacetic acid in water; dimethyl sulfoxide T=20°C; 15 h; Electrochemical reaction;

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Wang, Hai-Bin; Huang, Jing-Mei

Advanced Synthesis and Catalysis, 2016 , vol. 358, # 12 p. 1975 - 1981 Title/Abstract Full Text View citing articles Show Details

75%

Stage #1: Benzoylformic acid With potassium tert-butylate in ethanol

T=20°C; 2 h; Sealed tube; Stage #2: 2-amino-benzenethiol With dipotassium peroxodisulfate in acetonitrile

T=80°C; 8 h; Sealed tubeInert atmosphere;

Laha, Joydev K.; Patel, Ketul V.; Satyanarayana Tummalapalli; Dayal, Neetu

Chemical Communications, 2016 , vol. 52, # 67 p. 10245 - 10248 Title/Abstract Full Text View citing articles Show Details

32%

With tris(1,10-phenanthroline)ruthenium(II) dichloride; oxygen in dimethyl sulfoxide

T=32°C; 36 h; IrradiationSchlenk technique;

Liu, Jie; Liu, Qiang; Yi, Hong; Qin, Chu; Bai, Ruopeng; Qi, Xiaotian; Lan, Yu; Lei, Aiwen

Angewandte Chemie - International Edition, 2014 , vol. 53, # 2 p. 502 - 506 Angew. Chem., 2014 , vol. 126, # 2 p. 512 - 516,5 Title/Abstract Full Text View citing articles Show Details

Hide Details

With air

T=150°C;

Rabilloud,G. et al.

Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques, 1970 , vol. 270, p. 2019 - 2021 Full Text View citing articles Show Details

226

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Rx-ID: 1322465

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78%

With dmap; dicyclohexyl-carbodiimide in dichloromethane

T=20°C;

Cai, Feng; Pu, Xiaotao; Qi, Xiangbing; Lynch, Vincent; Radha, Akella; Ready, Joseph M.

Journal of the American Chemical Society, 2011 , vol. 133, # 45 p. 18066 - 18069 Title/Abstract Full Text View citing articles Show Details

With sulfuric acid

Huyser,E.S.; Neckers,D.C.

Journal of Organic Chemistry, 1964 , vol. 29, p. 276 - 278 Full Text View citing articles Show Details


With toluene-4-sulfonic acid in toluene

18 h; Reflux;

Bartrum, Hannah E.; Blakemore, David C.; Moody, Christopher J.; Hayes, Christopher J.

Chemistry - A European Journal, 2011 , vol. 17, # 35 p. 9586 - 9589 Title/Abstract Full Text View citing articles Show Details

Hide Details

With dmap; dicyclohexyl-carbodiimide in dichloromethane

T=0 - 20°C; 16.0833 h; Inert atmosphere;

Nicolle, Simon M.; Hayes, Christopher J.; Moody, Christopher J.

Chemistry - A European Journal, 2015 , vol. 21, # 12 p. 4576 - 4579 Title/Abstract Full Text View citing articles Show Details

227

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97%

With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide in ethyl acetate

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Rx-ID: 3409338

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Zhang, Shuai; Guo, Li-Na; Wang, Hua; Duan, Xin-Hua

Organic and Biomolecular Chemistry, 2013 , vol. 11, # 26 p. 4308 - 4311 Title/Abstract Full Text View citing articles Show Details

95%

With oxygen; copper(II) sulfate in dimethyl sulfoxide

T=120°C; 24 h;

Song, Qiuling; Feng, Qiang; Zhou, Mingxin

Organic Letters, 2013 , vol. 15, # 23 p. 5990 - 5993 Title/Abstract Full Text View citing articles Show Details

95%

With oxygen; copper diacetate in dimethyl sulfoxide

T=120°C; Sealed tube;

Feng, Qiang; Song, Qiuling

Journal of Organic Chemistry, 2014 , vol. 79, # 4 p. 1867 - 1871 Title/Abstract Full Text View citing articles Show Details

Hide Details

95%

With tert.-butylhydroperoxide; tetra-(n-butyl)ammonium iodide in ethyl acetate

T=80°C; 24 h;

Chang, Li-Ming; Yuan, Gao-Qing

Tetrahedron, 2016 , vol. 72, # 44 p. 7003 - 7007 Title/Abstract Full Text Show Details

88%

With 2-diazo-1,2-diphenylethan-1-one; methylene blue in pyridine; acetonitrile

1.33333 h; Irradiationoxidative decarboxylation of α-keto carboxylic acids;

Ando, Wataru; Miyazaki, Hajime; Akasaka, Takeshi

Tetrahedron Letters, 1982 , vol. 23, # 11 p. 1197 - 1200 Title/Abstract Full Text View citing articles Show Details

87%

With iodine; oxygen in ethyl acetate

24 h; Mercury lamp irradiation;

Tada, Norihiro; Shomura, Motoki; Cui, Lei; Nobuta, Tomoya; Miura, Tsuyoshi; Itoh, Akichika

Synlett, 2011 , # 19 art. no. U06311ST, p. 2896 - 2900 Title/Abstract Full Text View citing articles Show Details

81%

With menadione; sodium hydrogencarbonate; sodium Lascorbate in ethanol; water

T=20°C; P=760.051 Torr; pH=8.5; 24 h; DarknessGreen chemistry;

Silveira-Dorta, Gastn; Monzn, Diego M.; Crisstomo, Fernando P.; Martn, Toms; Martn, Vctor S.; Carrillo, Romen

Chemical Communications, 2015 , vol. 51, # 32 p. 7027 - 7030 Title/Abstract Full Text View citing articles Show Details

75%

With iodosylbenzene in 1,4-dioxane

Ambient temperature;

Moriarty, Robert M.; Gupta, Satish C.; Hu, Henry; Berenschot, Daniel M.; White, Kenneth B.

Journal of the American Chemical Society, 1981 , vol. 103, # 3 p. 686 - 688 Title/Abstract Full Text View citing articles Show Details


62%

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,3-bis(2,4,6trimethylphenyl)-4,5-dihydroimidazolium chloride in tetrahydrofuran

T=20°C; 16 h; Inert atmosphere;

Nair, Vijay; Varghese, Vimal; Paul, Rony Rajan; Jose, Anu; Sinu; Menon, Rajeev S.

Organic Letters, 2010 , vol. 12, # 11 p. 2653 - 2655 Title/Abstract Full Text View citing articles Show Details

44%

With water; oxygen in ethyl acetate

10 h; Irradiation;

Yamaguchi, Tomoaki; Nobuta, Tomoya; Kudo, Yasuhisa; Hirashima, Shin-Ichi; Tada, Norihiro; Miura, Tsuyoshi; Itoh, Akichika

Synlett, 2013 , vol. 24, # 5 art. no. ST-2013-U0018-L, p. 607 - 610 Title/Abstract Full Text View citing articles Show Details

With sodium hypochlorite; potassium nitrate

T=35°C; var. pH; Rate constant;

Elmore, P. R.; Reed, R. T.; Terkle-Huslig, T.; Welch, J. S.; Young, S. M.; Landolt, R. G.

Journal of Organic Chemistry, 1989 , vol. 54, # 4 p. 970 - 972 Title/Abstract Full Text View citing articles Show Details

With dihydrogen peroxide

pH=7.4; 0.333333 h; HEPES bufferInert atmosphere; Kinetics;

Lippert, Alexander R.; Keshari, Kayvan R.; Kurhanewicz, John; Chang, Christopher J.

Journal of the American Chemical Society, 2011 , vol. 133, # 11 p. 3776 - 3779 Title/Abstract Full Text View citing articles Show Details

With dihydrogen peroxide; N-2-hydroxyethylpiperazine-N'-2ethanesulfonic acid

pH=7.4; Kinetics; Hide Experimental Procedure

THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; CHANG, Christopher J.; LIPPERT, Alexander R.

Patent: WO2012/27274 A2, 2012 ; Location in patent: Page/Page column 29; 30 ; Title/Abstract Full Text Show Details

4:

A series of compounds were synthesized and kinetically analyzed (Table 1). The measured rate constants correlate well with the Hammett σ parameters giving a p value of 3.80 (Figure 4). Many of the compounds display faster reactivity with Η202 than BFA.

228

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Rx-ID: 9147834

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229

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91%

With silver carbonate in acetonitrile

T=60°C; 1 h;

Cheng, Kai; Zhao, Baoli; Qi, Chenze

RSC Advances, 2014 , vol. 4, # 89 p. 48698 - 48702 Title/Abstract Full Text View citing articles Show Details

75 % Chromat.

With dicarbonic acid,dimethyl ester; tetrakis(triphenylphosphine) palladium(0) in 1,4-dioxane

T=80°C; 6 h;

Yamamoto; Kakino; Narahashi; Shimizu

Bulletin of the Chemical Society of Japan, 2002 , vol. 75, # 6 p. 1333 - 1345 Title/Abstract Full Text View citing articles Show Details


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Rx-ID: 10060508

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92%

With C8F17SO3H in 1,2-dichloro-ethane

T=60°C; 24 h;

Yang, Yong-Hua; Liu, Ying-Hao; Shi, Min

Organic and Biomolecular Chemistry, 2006 , vol. 4, # 22 p. 4131 - 4134 Title/Abstract Full Text View citing articles Show Details

76%

With trimethylsilyl trifluoromethanesulfonate in 1,2-dichloroethane

T=60°C; 24 h;

Yang, Yong-Hua; Shi, Min

Journal of Organic Chemistry, 2005 , vol. 70, # 24 p. 10082 - 10085 Title/Abstract Full Text View citing articles Show Details

230

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Rx-ID: 22843468

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With acetic acid in ethanol

T=20°C; 16 h; Hide Experimental Procedure

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MERCK PATENT GMBH

Patent: WO2003/104205 A1, 2003 ; Location in patent: Page 101 ; Title/Abstract Full Text Show Details

4.1:Beispiel 4

Zu einer Loesung von 600 mg (4) in [ETHANOL/EISESSIG] gibt man 293 mg [BENZOYLAMEISENSaeURE] und ruehrt 16 Stunden bei Raumtemperatur. Das Loesungsmittel wird abdestilliert, der Rueckstand wird mit Ether aufgeruehrt, abgesaugt und mit Ether gewaschen. Man erhaelt 800 mg der Verbindung [{2- [3- (3-ETHOXY-4-METHOXY-PHENYL)-5,] 6- [DIHYDRO-4H-PYRIDAZIN-1-YL]-2-OXO-ETHOXYIMINO}-2-PHENYL-ESSIGSaeURE] [(I-D-1] ; Tabelle 2).

231

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Rx-ID: 23051545

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With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)carbodiimide hydrochloride in DMF (N,N-dimethyl-formamide)

T=20°C; 14 h; Hide Experimental Procedure

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Japan Tobacco Inc.

Patent: EP1452526 A1, 2004 ; Location in patent: Page 118 ; Title/Abstract Full Text Show Details

5.4:Example 5-45-chloro-1H-indole-2-carboxylic acid 2-(benzoylformyl)hydrazide

To a suspension (5 ml) of 5-chloro-1H-indole-2-carboxylic acid hydrazide obtained in Example 1 a) (240 mg) and benzoylformic acid (150 mg) in DMF were added 1-hydroxybenzotriazole (184 mg) and EDC (230 mg). The mixture was stirred at room temperature for 14 hr and water was added to the reaction solution. This mixture was extracted with ethyl acetate. The organic layer was washed successively with 10percent aqueous citric acid solution, saturated aqueous sodium hydrogen carbonate, water and saturated brine, and dried over sodium sulfate. This solution was filtered and concentrated under reduced pressure. The residue was washed with diethyl ether to give the title compound (106 mg) (see Table 28).


232

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Rx-ID: 23744324

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With dicyclohexyl-carbodiimide in acetone; benzene

T=0 - 20°C; Hide Experimental Procedure

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Huang, Yazhong; Hu, Shuanghua; Degnan, Andrew P.

Patent: US2006/20019 A1, 2006 ; Location in patent: Page/Page column 11 ; Title/Abstract Full Text Show Details

32:

Benzoylformic acid in acetone (3.00 g, 20 ml) was mixed with 3,5-bistrifluoromethylbenzylamine (tech. grade, 80percent, 5.85 g, 1 equivalent) in benzene (20 ml). The resultant suspension was stirred at 0° C., and a suspension of DCC in benzene (4.34 g, 1.1 equivalents, 20 ml) was added slowly. The reaction mixture was allowed to warm up to RT and stirred overnight. The reaction mixture was quenched with brine and extracted with EtOAc. After concentration, the residue was purified by flash chromatography on silica gel to give 3.69 g of N(3,5-bis(trifluoromethyl)benzyl-2-oxo-2-phenylacetamide as a yellow solid. 1H NMR (500 MHz, DMSO-D6) δ ppm 9.62 (1H, t, J=5.80 Hz) 8.07 (2H, s) 8.05 (1H, s) 7.97-8.01 (2H, m) 7.75 (1H, t, J=7.32 Hz) 7.59 (2H, t, J=7.93 Hz) 4.67 (2H, d, J=6.10 Hz). MS [ESI, MH+] m/z calcd for C17H12F6NO2 376.08, found 376.07.

233

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Rx-ID: 28008489

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With 1- hydroxybenzotriazole; 1-ethyl-(3-(3dimethylamino)propyl)-carbodiimide hydrochloride; N,Ndiisopropylethylamine in dichloromethane

T=20°C; 16 h; Hide Experimental Procedure

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Theravance, Inc.

Patent: US2008/269190 A1, 2008 ; Location in patent: Page/Page column 30 ; Title/Abstract Full Text Show Details

5:

1-(4-Dimethylamino-piperidin-1-yl)-2-phenylethane-1,2-dione (5a): Benzoylformic acid (1.0 g, 6.7 mmol), dimethylpiperidin-4-ylamine (854 mg, 6.7 mmol), DIPEA (3.5 mL, 20.0 mmol), and 1-hydroxybenzotriazole (1.4 g, 10 mmol) were dissolved in 20 mL of methylene chloride, then N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide hydrochloride (1.53 g, 7.99 mmol) was added and the mixture was stirred at room temperature for 16 hours. The mixture was extracted with a 1.0 N NaOH solution, then the organic layer was dried over Na2SO4 and concentrated. The crude product was purified by column chromatography (10-30percent MeOH in methylene chloride gradient) to give intermediate (5a) (501 mg).

234


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Rx-ID: 28470346

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Stage #1: α-ketophenylacetic acid With HATU in N,N-dimethylformamide

T=25°C; 0.25 h; Stage #2: PP2 With N-ethyl-N,N-diisopropylamine in N,Ndimethyl-formamide

T=25°C; 16 h; Hide Experimental Procedure

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FOLDRX PHARMACEUTICALS, INC.

Patent: WO2009/62118 A2, 2009 ; Location in patent: Page/Page column 232-233 ; Title/Abstract Full Text Show Details

68:

To a dry, round bottom flask was added benzoylfomic acid (99 mg, 0.66 mmol), ηATU(252 mg, 0.66 mmol), and dimethylformamide (3 ml). This solution was stirred at 25 °C for 15 min, followed by addition of l-feτt-butyl-3 -(4-chloro-phenyl)- 1 H-pyrazolo [3,4-cf]pyrimidin-4ylamine (lOOmg, 0.33 mmol) and DIEA (220 μL, 1.33 mmol). The resulting mixture was stirred at 25 0C for 16 hr. The crude material was purified via reverse phase preparative ηPLC-MS, <n="234"/>concentrated, and triturated with acetonitrile to afford the title compound (17 mg, 0.04 mmol); LC/MS, API-ES, Pos, (M+H)+, 434.9, 436.9.

235

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Rx-ID: 28907908

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With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in dichloromethane

T=0 - 20°C; 12 h; Inert atmosphere; Hide Experimental Procedure

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Knust, Henner; Nettekoven, Matthias; Pinard, Emmanuel; Roche, Olivier; Rogers-Evans, Mark

Patent: US2009/312314 A1, 2009 ; Location in patent: Page/Page column 41 ; Title/Abstract Full Text Show Details

47.c.3:

To a solution of (1-ethyl-3-methyl-1H-pyrazol-4-yl)-[2-(6-trifluoromethyl-pyridin-3-yl)-ethyl]-amine (100 mg) in CH2Cl2 (5 mL) was added under a nitrogen atmosphere at 0° C. benzoyl formic acid (1.1 eq., commercially available) and EDC (1.1 eq). After stirring for 12 h a rt, the mixture was washed with aqueous Na2CO3 (saturated, 2.5 mL) and water (2.5 mL), the combined aqueous layers were extracted with CH2Cl2 (3.x.2.5 mL) and the combined organic layers dried over sodium sulfate. Concentration afforded the title compound (161 mg, >100percent) as a light yellow oil which was used without further purification for the next step. MS m/e: 431.2 [M+H]+.

236


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Rx-ID: 29050120

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96%

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Stage #1: α-ketophenylacetic acid With oxalyl dichloride; N,Ndimethyl-formamide in chloroform

T=0 - 20°C; Stage #2: (3R)-3-hydroxy-1-azabicyclo[2.2.2]octane in chloroform

T=20°C;

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Prat, Maria; Fernandez, Dolors; Buil, M. Antonia; Crespo, Maria I.; Casals, Gaspar; Ferrer, Manuel; Tort, Laia; Castro, Jordi; Monleon, Juan M.; Gavalda, Amadeu; Miralpeix, Montserrat; Ramos, Israel; Domenech, Teresa; Vilella, Dolors; Anton, Francisca; Huerta, Josep M.; Espinosa, Sonia; Lopez, Manuel; Sentellas, Sonia; Gonzalez, Marisa; Alberti, Joan; Segarra, Victor; Cardenas, Alvaro; Beleta, Jorge; Ryder, Hamish

Journal of Medicinal Chemistry, 2009 , vol. 52, # 16 p. 5076 - 5092 Title/Abstract Full Text View citing articles Show Details

237

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Rx-ID: 29691244

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84%

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With dipotassium peroxodisulfate; bis(benzonitrile)palladium(II) dichloride; silver(l) oxide in 1,4-dioxane; acetic acid; dimethyl sulfoxide

T=120°C; 12 h;

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Li, Mingzong; Ge, Haibo

Organic Letters, 2010 , vol. 12, # 15 p. 3464 - 3467 Title/Abstract Full Text View citing articles Show Details

238

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Rx-ID: 29691254

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83%

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With dipotassium peroxodisulfate; bis(benzonitrile)palladium(II) dichloride; silver(l) oxide in 1,4-dioxane; acetic acid; dimethyl sulfoxide

T=120°C; 12 h;

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Li, Mingzong; Ge, Haibo

Organic Letters, 2010 , vol. 12, # 15 p. 3464 - 3467 Title/Abstract Full Text View citing articles Show Details


239

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Rx-ID: 29691255

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77%

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With dipotassium peroxodisulfate; bis(benzonitrile)palladium(II) dichloride; silver(l) oxide in 1,4-dioxane; acetic acid; dimethyl sulfoxide

T=120°C; 12 h;

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Li, Mingzong; Ge, Haibo

Organic Letters, 2010 , vol. 12, # 15 p. 3464 - 3467 Title/Abstract Full Text View citing articles Show Details

240

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Rx-ID: 30125543

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79%

With dicyclohexyl-carbodiimide in dichloromethane

T=-60°C; 4.16667 h;

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Zhang, Zhiguo; Zhang, Qian; Ni, Zhikun; Liu, Qun

Chemical Communications, 2010 , vol. 46, # 8 p. 1269 - 1271 Title/Abstract Full Text View citing articles Show Details

241

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Rx-ID: 30786416

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83%

With dipotassium peroxodisulfate; palladium diacetate in water; dimethyl sulfoxide

T=20°C; 3 h;

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Li, Mingzong; Wang, Cong; Ge, Haibo

Organic Letters, 2011 , vol. 13, # 8 p. 2062 - 2064 Title/Abstract Full Text View citing articles Show Details


242

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Rx-ID: 30786433

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82%

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With dipotassium peroxodisulfate; palladium diacetate in water; dimethyl sulfoxide

T=20°C; 3 h;

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Li, Mingzong; Wang, Cong; Ge, Haibo

Organic Letters, 2011 , vol. 13, # 8 p. 2062 - 2064 Title/Abstract Full Text View citing articles Show Details

243

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Rx-ID: 30786438

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79%

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With dipotassium peroxodisulfate; palladium diacetate in water; dimethyl sulfoxide

T=20°C; 3 h;

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Li, Mingzong; Wang, Cong; Ge, Haibo

Organic Letters, 2011 , vol. 13, # 8 p. 2062 - 2064 Title/Abstract Full Text View citing articles Show Details

244

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Rx-ID: 34021559

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82%

With Fe(III)(edta); dihydrogen peroxide; palladium diacetate; sodium hydroxide in water

T=20°C; pH=7.2 - 7.8; 0.416667 h;

Sharma, Sugandha; Khan, Imran A.; Saxena, Anil K.

Advanced Synthesis and Catalysis, 2013 , vol. 355, # 4 p. 673 - 678 Title/Abstract Full Text View citing articles Show Details

60%

With dipotassium peroxodisulfate; palladium diacetate; silver(l)

Wang, Hua; Guo, Li-Na; Duan, Xin-Hua


oxide in dimethyl sulfoxide; N,N-dimethyl-formamide

T=20°C; Inert atmosphere;

Organic Letters, 2012 , vol. 14, # 17 p. 4358 - 4361 Title/Abstract Full Text View citing articles Show Details

245

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Rx-ID: 34021642

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86%

With Fe(III)(edta); dihydrogen peroxide; palladium diacetate; sodium hydroxide in water

T=20°C; pH=7.2 - 7.8; 0.166667 h;

Sharma, Sugandha; Khan, Imran A.; Saxena, Anil K.

Advanced Synthesis and Catalysis, 2013 , vol. 355, # 4 p. 673 - 678 Title/Abstract Full Text View citing articles Show Details

61%

With dipotassium peroxodisulfate; palladium diacetate; silver(l) oxide in dimethyl sulfoxide; N,N-dimethyl-formamide

T=20°C; Inert atmosphere;

Wang, Hua; Guo, Li-Na; Duan, Xin-Hua

Organic Letters, 2012 , vol. 14, # 17 p. 4358 - 4361 Title/Abstract Full Text View citing articles Show Details

246

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Rx-ID: 35820814

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81%

With palladium (II) trifluoroacetate; silver carbonate in ethylene glycol dimethyl ether

T=165°C; 24 h; Sealed tube; chemoselective reaction;

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Miao, Jinmin; Ge, Haibo

Organic Letters, 2013 , vol. 15, # 12 p. 2930 - 2933 Title/Abstract Full Text View citing articles Show Details

247

Rx-ID: 35820821

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75%

With palladium (II) trifluoroacetate; silver carbonate in ethylene glycol dimethyl ether

T=150°C; 48 h; Sealed tube; chemoselective reaction;

Miao, Jinmin; Ge, Haibo

Organic Letters, 2013 , vol. 15, # 12 p. 2930 - 2933 Title/Abstract Full Text View citing articles Show Details

248

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Rx-ID: 35820830

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80%

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With palladium (II) trifluoroacetate; silver carbonate in ethylene glycol dimethyl ether

T=150°C; 24 h; Sealed tube; Reagent/catalystConcentrationSolvent; chemoselective reaction;

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Miao, Jinmin; Ge, Haibo

Organic Letters, 2013 , vol. 15, # 12 p. 2930 - 2933 Title/Abstract Full Text View citing articles Show Details

249

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Rx-ID: 36327892

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7 g

Stage #1: in ethanol

T=25°C; 2 h; Stage #2: With sodium carbonate in ethanol

T=25°C; 2 h; Hide Experimental Procedure

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Melnicky, Radek; Grepl, Martin; Lycka, Antonin; Bertolasi, Valerio; Kvapil, Lubomir; Dvorakova, Barbora; Hradil, Pavel

Synthesis (Germany), 2013 , vol. 45, # 17 art. no. SS-2012-Z1009-OP, p. 2447 - 2457 Title/Abstract Full Text View citing articles Show Details

Sodium (2E)-(2-Arylhydrazono)propanoates 10a–e and (2Z)-Sodium Aryl(arylhydrazono)acetates 10f–l; General Procedure

General procedure: Derivatives 8a–g (45.4 mmol) were dissolved in EtOH (30.0 mL). Arylhydrazine derivatives 9a–g (45.4 mmol) were added, and the mixture was stirred at 25 °C for 1–8 h (Table 5) (TLC monitoring, n-hexanes–EtOAc, 7:3). Then Na2CO3 (2.4 g, 22.7 mmol) was added and the mixture was stirred at 25 °C for 2 h. The solid precipitate was filtered off, washed with EtOH, and dried in a vacuum drier. Compounds 10a–g were obtained as yellow solids and used in the next step without purification.

250


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Rx-ID: 36327893

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5.6 g

Stage #1: in ethanol

T=25°C; 1.5 h; Stage #2: With sodium carbonate in ethanol

T=25°C; 2 h; Hide Experimental Procedure

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Melnicky, Radek; Grepl, Martin; Lycka, Antonin; Bertolasi, Valerio; Kvapil, Lubomir; Dvorakova, Barbora; Hradil, Pavel

Synthesis (Germany), 2013 , vol. 45, # 17 art. no. SS-2012-Z1009-OP, p. 2447 - 2457 Title/Abstract Full Text View citing articles Show Details

Sodium (2E)-(2-Arylhydrazono)propanoates 10a–e and (2Z)-Sodium Aryl(arylhydrazono)acetates 10f–l; General Procedure

General procedure: Derivatives 8a–g (45.4 mmol) were dissolved in EtOH (30.0 mL). Arylhydrazine derivatives 9a–g (45.4 mmol) were added, and the mixture was stirred at 25 °C for 1–8 h (Table 5) (TLC monitoring, n-hexanes–EtOAc, 7:3). Then Na2CO3 (2.4 g, 22.7 mmol) was added and the mixture was stirred at 25 °C for 2 h. The solid precipitate was filtered off, washed with EtOH, and dried in a vacuum drier. Compounds 10a–g were obtained as yellow solids and used in the next step without purification.

251

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Rx-ID: 36327894

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8.2 g

Stage #1: in ethanol

T=25°C; 1 h; Stage #2: With sodium carbonate in ethanol

T=25°C; 2 h; Hide Experimental Procedure

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Melnicky, Radek; Grepl, Martin; Lycka, Antonin; Bertolasi, Valerio; Kvapil, Lubomir; Dvorakova, Barbora; Hradil, Pavel

Synthesis (Germany), 2013 , vol. 45, # 17 art. no. SS-2012-Z1009-OP, p. 2447 - 2457 Title/Abstract Full Text View citing articles Show Details

Sodium (2E)-(2-Arylhydrazono)propanoates 10a–e and (2Z)-Sodium Aryl(arylhydrazono)acetates 10f–l; General Procedure

General procedure: Derivatives 8a–g (45.4 mmol) were dissolved in EtOH (30.0 mL). Arylhydrazine derivatives 9a–g (45.4 mmol) were added, and the mixture was stirred at 25 °C for 1–8 h (Table 5) (TLC monitoring, n-hexanes–EtOAc, 7:3). Then Na2CO3 (2.4 g, 22.7 mmol) was added and the mixture was stirred at 25 °C for 2 h. The solid precipitate was filtered off, washed with EtOH, and dried in a vacuum drier. Compounds 10a–g were obtained as yellow solids and used in the next step without purification.

252


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Rx-ID: 36327895

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6.4 g

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Melnicky, Radek; Grepl, Martin; Lycka, Antonin; Bertolasi, Valerio; Kvapil, Lubomir; Dvorakova, Barbora; Hradil, Pavel

Synthesis (Germany), 2013 , vol. 45, # 17 art. no. SS-2012-Z1009-OP, p. 2447 - 2457 Title/Abstract Full Text View citing articles Show Details

Stage #1: in ethanol

T=25°C; 1 h; Stage #2: With sodium carbonate in ethanol

T=25°C; 2 h; Hide Experimental Procedure

Sodium (2E)-(2-Arylhydrazono)propanoates 10a–e and (2Z)-Sodium Aryl(arylhydrazono)acetates 10f–l; General Procedure

General procedure: Derivatives 8a–g (45.4 mmol) were dissolved in EtOH (30.0 mL). Arylhydrazine derivatives 9a–g (45.4 mmol) were added, and the mixture was stirred at 25 °C for 1–8 h (Table 5) (TLC monitoring, n-hexanes–EtOAc, 7:3). Then Na2CO3 (2.4 g, 22.7 mmol) was added and the mixture was stirred at 25 °C for 2 h. The solid precipitate was filtered off, washed with EtOH, and dried in a vacuum drier. Compounds 10a–g were obtained as yellow solids and used in the next step without purification.

253

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Rx-ID: 36327896

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Melnicky, Radek; Grepl, Martin; Lycka, Antonin; Bertolasi, Valerio; Kvapil, Lubomir; Dvorakova, Barbora; Hradil, Pavel

Synthesis (Germany), 2013 , vol. 45, # 17 art. no. SS-2012-Z1009-OP, p. 2447 - 2457 Title/Abstract Full Text View citing articles Show Details

Stage #1: in ethanol

T=25°C; 1.5 h; Stage #2: With sodium carbonate in ethanol

T=25°C; 2 h; Hide Experimental Procedure

Sodium (2E)-(2-Arylhydrazono)propanoates 10a–e and (2Z)-Sodium Aryl(arylhydrazono)acetates 10f–l; General Procedure

General procedure: Derivatives 8a–g (45.4 mmol) were dissolved in EtOH (30.0 mL). Arylhydrazine derivatives 9a–g (45.4 mmol) were added, and the mixture was stirred at 25 °C for 1–8 h (Table 5) (TLC monitoring, n-hexanes–EtOAc, 7:3). Then Na2CO3 (2.4 g, 22.7 mmol) was added and the mixture was stirred at 25 °C for 2 h. The solid precipitate was filtered off, washed with EtOH, and dried in a vacuum drier. Compounds 10a–g were obtained as yellow solids and used in the next step without purification.

254

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Rx-ID: 37206973

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92%

With trifluoroacetic acid in isopropyl alcohol

T=70°C; 18 h;

Yan, Shaoxi; Ye, Leping; Liu, Miaochang; Chen, Jiuxi; Ding, Jinchang; Gao, Wenxia; Huang, Xiaobo; Wu, Huayue

RSC Advances, 2014 , vol. 4, # 32 p. 16705 - 16709 Title/Abstract Full Text View citing articles Show Details

90%

With Oxonereg; in diethylene glycol dimethyl ether; dimethyl sulfoxide

T=120°C; 12 h; Reagent/catalystSolvent;

Wang, Hua; Yang, Hua; Li, Yiping; Duan, Xin-Hua

RSC Advances, 2014 , vol. 4, # 17 p. 8720 - 8722 Title/Abstract Full Text View citing articles Show Details


255

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Rx-ID: 37206975

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93%

With trifluoroacetic acid in isopropyl alcohol

T=70°C; 18 h;

Yan, Shaoxi; Ye, Leping; Liu, Miaochang; Chen, Jiuxi; Ding, Jinchang; Gao, Wenxia; Huang, Xiaobo; Wu, Huayue

RSC Advances, 2014 , vol. 4, # 32 p. 16705 - 16709 Title/Abstract Full Text View citing articles Show Details

87%

With Oxonereg; in diethylene glycol dimethyl ether; dimethyl sulfoxide

T=120°C; 12 h;

Wang, Hua; Yang, Hua; Li, Yiping; Duan, Xin-Hua

RSC Advances, 2014 , vol. 4, # 17 p. 8720 - 8722 Title/Abstract Full Text View citing articles Show Details

256

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Rx-ID: 37206978

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86%

With trifluoroacetic acid in isopropyl alcohol

T=70°C; 18 h;

Yan, Shaoxi; Ye, Leping; Liu, Miaochang; Chen, Jiuxi; Ding, Jinchang; Gao, Wenxia; Huang, Xiaobo; Wu, Huayue

RSC Advances, 2014 , vol. 4, # 32 p. 16705 - 16709 Title/Abstract Full Text View citing articles Show Details

76%

With Oxonereg; in diethylene glycol dimethyl ether; dimethyl sulfoxide

T=120°C; 12 h;

Wang, Hua; Yang, Hua; Li, Yiping; Duan, Xin-Hua

RSC Advances, 2014 , vol. 4, # 17 p. 8720 - 8722 Title/Abstract Full Text View citing articles Show Details

257

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Rx-ID: 37206979

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94%

With trifluoroacetic acid in isopropyl alcohol

T=70°C; 18 h; SolventReagent/catalystTemperature;

Yan, Shaoxi; Ye, Leping; Liu, Miaochang; Chen, Jiuxi; Ding, Jinchang; Gao, Wenxia; Huang, Xiaobo; Wu, Huayue

RSC Advances, 2014 , vol. 4, # 32 p. 16705 - 16709 Title/Abstract Full Text View citing articles Show Details

80%

With Oxonereg; in diethylene glycol dimethyl ether; dimethyl sulfoxide

T=120°C; 12 h;

Wang, Hua; Yang, Hua; Li, Yiping; Duan, Xin-Hua

RSC Advances, 2014 , vol. 4, # 17 p. 8720 - 8722 Title/Abstract Full Text View citing articles Show Details

258

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Rx-ID: 37453151

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Stage #1: α-ketophenylacetic acid With 1-hydroxy-pyrrolidine2,5-dione; dicyclohexyl-carbodiimide in dichloromethane; N,Ndimethyl-formamide

T=50°C; 0.5 h; Stage #2: N-tert-Butoxycarbonyl-L-Lysine With triethylamine in dichloromethane; N,N-dimethyl-formamide

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ALLOZYNE, INC; TEUTEN, Andrew; GRABSTEIN, Kenneth H.; VAN BRUNT, Michael; MARELLI, Marcello

Patent: WO2014/44873 A1, 2014 ; Location in patent: Page/Page column 17 ; Title/Abstract Full Text Show Details

Stage #3: With hydrogenchloride in 1,4-dioxane; acetonitrile

2 h; Hide Experimental Procedure

Preparation of Preparation of (S)-2-amino-6((2-oxo-2-phenylacetamide)hexanoic acid (Formula V.6)

In a 50mL round bottomed flask with magnetic stirrer was dissolved pyruvic acid (3.5g, 23.3mmol) in a 2:1 mixture of dichloromethane and DMF (20mL). To this mixture was added DCC (5.7g, 27.6mmol) and NHS (3.2g, 27.6mmol). The mixture was heated to 50C for 30min with stirring. The solution was allowed to cool and then added through a filter to a suspension of N-Boc-Lysine (5.2g, 21.2mmol) in DMF (20mL) in a separate lOOmL round bottomed flask with magnetic stirrer. Triethyl amine (8.8mL, 63.6mmol) was added after addition of the activated ester, and the mixture was stirred overnight. The mixture was partitioned between ethyl acetate and citric acid. The layers were separated and the aqueous layer was extracted 4 times with ethyl acetate. The organic layers were combined, dried over sodium sulfate and concentrated. The resulting residue was further purified by flash chromatography to afford the final N-Boc lysine derivative as an oil. In a lOOmL roundbottomed flask was placed the keto-N-Boc lysine derivative (4g, 10.6mmol) in acetonitrile (50mL). To this was added a solution of hydrochloric acid (15mL, 4N in dioxane). The solution was stirred for 2h and concentrated. Final purification by flash chromatography afforded the target amino acid. Analytical MS : m/z (ES+) expected 278.1 (M+H)+, found 279.2.

259

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Rx-ID: 38124592

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75%

Stage #1: α-ketophenylacetic acid With dichloromethoxy methane in dichloromethane

T=20°C; 1 h; Inert atmosphere; Stage #2: N-benzyl-2-ethynylaniline With 4-(N,Ndimethlyamino)pyridine; triethylamine in dichloromethane

T=0 - 20°C; 24 h; Inert atmosphere;

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Kondoh, Azusa; Aoki, Takuma; Terada, Masahiro

Organic Letters, 2014 , vol. 16, # 13 p. 3528 - 3531 Title/Abstract Full Text View citing articles Show Details


260

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Rx-ID: 38591773

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83%

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With palladium diacetate; silver carbonate in 1,2-dichlorobenzene

T=100°C; 24 h; Inert atmosphere;

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Wang, Yong; Kang, Qiang

Organic Letters, 2014 , vol. 16, # 16 p. 4190 - 4193 Title/Abstract Full Text View citing articles Show Details

261

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Rx-ID: 39631199

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95%

With dipotassium peroxodisulfate in water; acetonitrile

T=70°C; 24 h; Inert atmosphereSchlenk techniqueSealed tube;

Yan, Kelu; Yang, Daoshan; Wei, Wei; Zhao, Jing; Shuai, Yuanyuan; Tian, Laijin; Wang, Hua

Organic and Biomolecular Chemistry, 2015 , vol. 13, # 26 p. 7323 - 7330 Title/Abstract Full Text View citing articles Show Details

74%

With ammonium peroxydisulfate; copper(II) oxide in water; dimethyl sulfoxide

T=80°C; 12 h;

Rong, Guangwei; Mao, Jincheng; Liu, Defu; Yan, Hong; Zheng, Yang; Chen, Jie

RSC Advances, 2015 , vol. 5, # 34 p. 26461 - 26464 Title/Abstract Full Text View citing articles Show Details

262

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Rx-ID: 39631200

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99%

With dipotassium peroxodisulfate in water; acetonitrile

T=70°C; 24 h; Inert atmosphereSchlenk techniqueSealed tube;

Yan, Kelu; Yang, Daoshan; Wei, Wei; Zhao, Jing; Shuai, Yuanyuan; Tian, Laijin; Wang, Hua

Organic and Biomolecular Chemistry, 2015 , vol. 13, # 26 p. 7323 - 7330 Title/Abstract Full Text View citing articles Show Details

73%

With ammonium peroxydisulfate; copper(II) oxide in water; dimethyl sulfoxide

T=80°C; 12 h;

Rong, Guangwei; Mao, Jincheng; Liu, Defu; Yan, Hong; Zheng, Yang; Chen, Jie

RSC Advances, 2015 , vol. 5, # 34 p. 26461 - 26464 Title/Abstract Full Text View citing articles Show Details

263

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Rx-ID: 41079803

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75%

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With dipotassium hydrogenphosphate; C36H18F10IrN4(1+)*F6P(1-

) in dichloromethane; water

T=20°C; 9 h; Schlenk techniqueIrradiation;

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Wang, Guang-Zu; Shang, Rui; Cheng, Wan-Min; Fu, Yao

Organic Letters, 2015 , vol. 17, # 19 p. 4830 - 4833 Title/Abstract Full Text View citing articles Show Details

264

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Rx-ID: 41079810

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78%

With dipotassium hydrogenphosphate; C36H18F10IrN4(1+)*F6P(1-

) in dichloromethane; water

T=20°C; 9 h; Schlenk techniqueIrradiation;

265

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Synthesize Find similar

Wang, Guang-Zu; Shang, Rui; Cheng, Wan-Min; Fu, Yao

Organic Letters, 2015 , vol. 17, # 19 p. 4830 - 4833 Title/Abstract Full Text View citing articles Show Details


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Rx-ID: 41079817

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81%

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With dipotassium hydrogenphosphate; C36H18F10IrN4(1+)*F6P(1) in dichloromethane; water

T=20°C; 9 h; Schlenk techniqueIrradiation;

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Wang, Guang-Zu; Shang, Rui; Cheng, Wan-Min; Fu, Yao

Organic Letters, 2015 , vol. 17, # 19 p. 4830 - 4833 Title/Abstract Full Text View citing articles Show Details

266

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Rx-ID: 41276097

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85%

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With Ru(acetylacetonate)3; hydrogen; trifluoromethanesulfonimide; [2((diphenylphospino)methyl)-2-methyl-1,3propanediyl]bis[diphenylphosphine] in dibutyl ether

T=160°C; P=45004.5 Torr; 18 h; Autoclave;

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Sorribes, Ivn; Cabrero-Antonino, Jose R.; Vicent, Cristian; Junge, Kathrin; Beller, Matthias

Journal of the American Chemical Society, 2015 , vol. 137, # 42 p. 13580 - 13587 Title/Abstract Full Text View citing articles Show Details

267

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Rx-ID: 41644723

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75%

268

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With oxygen; palladium diacetate; eosin y in chlorobenzene

T=20°C; 15 h; Irradiation;

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Zhou, Chao; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Organic Letters, 2015 , vol. 17, # 24 p. 6198 - 6201 Title/Abstract Full Text View citing articles Show Details


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Rx-ID: 41644724

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81%

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With oxygen; palladium diacetate; eosin y in chlorobenzene

T=20°C; 15 h; Irradiation;

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Zhou, Chao; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Organic Letters, 2015 , vol. 17, # 24 p. 6198 - 6201 Title/Abstract Full Text View citing articles Show Details

269

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Rx-ID: 41644726

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82%

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With oxygen; palladium diacetate; eosin y in chlorobenzene

T=20°C; 15 h; Irradiation;

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Zhou, Chao; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Organic Letters, 2015 , vol. 17, # 24 p. 6198 - 6201 Title/Abstract Full Text View citing articles Show Details

270

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Rx-ID: 41644727

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76%

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With oxygen; palladium diacetate; eosin y in chlorobenzene

T=20°C; 15 h; Irradiation;

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Zhou, Chao; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Organic Letters, 2015 , vol. 17, # 24 p. 6198 - 6201 Title/Abstract Full Text View citing articles Show Details

271

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Synthesize Find similar


Rx-ID: 41644728

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75%

With oxygen; palladium diacetate; eosin y in chlorobenzene

T=20°C; 15 h; Irradiation;

Zhou, Chao; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Organic Letters, 2015 , vol. 17, # 24 p. 6198 - 6201 Title/Abstract Full Text View citing articles Show Details

272

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Rx-ID: 41644729

Find similar reactions

82%

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With oxygen; palladium diacetate; eosin y in chlorobenzene

T=20°C; 15 h; Irradiation;

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Zhou, Chao; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Organic Letters, 2015 , vol. 17, # 24 p. 6198 - 6201 Title/Abstract Full Text View citing articles Show Details

273

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Rx-ID: 41644730

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77%

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With oxygen; palladium diacetate; eosin y in chlorobenzene

T=20°C; 15 h; Irradiation;

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Zhou, Chao; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Organic Letters, 2015 , vol. 17, # 24 p. 6198 - 6201 Title/Abstract Full Text View citing articles Show Details

274

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Rx-ID: 41644734

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76%

With oxygen; palladium diacetate; eosin y in chlorobenzene

T=20°C; 15 h; Irradiation;

Zhou, Chao; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Organic Letters, 2015 , vol. 17, # 24 p. 6198 - 6201 Title/Abstract Full Text View citing articles Show Details

275

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Rx-ID: 41644736

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82%

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With oxygen; palladium diacetate; eosin y in chlorobenzene

T=20°C; 15 h; Irradiation;

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Zhou, Chao; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Organic Letters, 2015 , vol. 17, # 24 p. 6198 - 6201 Title/Abstract Full Text View citing articles Show Details

276

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Rx-ID: 41644737

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77%

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With oxygen; palladium diacetate; eosin y in chlorobenzene

T=20°C; 15 h; Irradiation;

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Zhou, Chao; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Organic Letters, 2015 , vol. 17, # 24 p. 6198 - 6201 Title/Abstract Full Text View citing articles Show Details

277

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Rx-ID: 41644738

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76%

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With oxygen; palladium diacetate; eosin y in chlorobenzene

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Zhou, Chao; Li, Pinhua; Zhu, Xianjin; Wang, Lei


T=20°C; 15 h; Irradiation;

Organic Letters, 2015 , vol. 17, # 24 p. 6198 - 6201 Title/Abstract Full Text View citing articles Show Details

278

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Rx-ID: 41644739

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81%

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With oxygen; palladium diacetate; eosin y in chlorobenzene

T=20°C; 15 h; Irradiation;

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Zhou, Chao; Li, Pinhua; Zhu, Xianjin; Wang, Lei

Organic Letters, 2015 , vol. 17, # 24 p. 6198 - 6201 Title/Abstract Full Text View citing articles Show Details

279

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Rx-ID: 41722617

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With palladium(II) trifluoroacetate; silver carbonate in DME

T=150 - 165°C; regioselective reaction; Hide Experimental Procedure

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Pan, Shulei; Zhou, Bo; Zhang, Yanghui; Shao, Changdong; Shi, Guangfa

Synlett, 2016 , vol. 27, # 2 art. no. ST-2015-W0600-L, p. 277 - 281 Title/Abstract Full Text View citing articles Show Details

(20) Synthesis of para-Benzoylated Arenes

General procedure: A mixture of m-toluic acid (27.2 mg, 0.20 mmol), benzoylformicacid (90.1 mg, 0.60 mmol), Pd(TFA)2 (6.6 mg, 0.020 mmol), andAg2CO3 (165.5 mg, 0.60 mmol) in DME (2 mL) was heated at150–165 °C for 24–48 h. After cooling down to r.t., the reactionmixture was diluted by addition of EtOAc (10 mL) and then filteredthrough a pad of Celite. The filtrate was concentrated invacuo to afford 2-benzoylbenzoic acid derivatives. A mixture ofthe crude product, Cu2O (1.4 mg, 0.010 mmol), and 1,10-phenanthroline (3.6 mg, 0.020 mmol) in a solution of NMP (1.5mL) and quinoline (0.5 mL) was heated under an atmosphere ofN2 at 170 °C for 24 h. The reaction mixture was quenched byaddition of 0.2 M aq HCl (10 mL), diluted with EtOAc (10 mL),and then filtered through a pad of Celite. The filtrate waswashed with brine (10 mL), dried over Na2SO4, and concentratedin vacuo. The residue was purified by silica gel preparativeTLC to give phenyl(p-tolyl)methanone.

280

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Synthesize Find similar


Rx-ID: 41722624

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With palladium(II) trifluoroacetate; silver carbonate in DME

T=150 - 165°C; regioselective reaction; Hide Experimental Procedure

Pan, Shulei; Zhou, Bo; Zhang, Yanghui; Shao, Changdong; Shi, Guangfa

Synlett, 2016 , vol. 27, # 2 art. no. ST-2015-W0600-L, p. 277 - 281 Title/Abstract Full Text View citing articles Show Details

(20) Synthesis of para-Benzoylated Arenes

General procedure: A mixture of m-toluic acid (27.2 mg, 0.20 mmol), benzoylformicacid (90.1 mg, 0.60 mmol), Pd(TFA)2 (6.6 mg, 0.020 mmol), andAg2CO3 (165.5 mg, 0.60 mmol) in DME (2 mL) was heated at150–165 °C for 24–48 h. After cooling down to r.t., the reactionmixture was diluted by addition of EtOAc (10 mL) and then filteredthrough a pad of Celite. The filtrate was concentrated invacuo to afford 2-benzoylbenzoic acid derivatives. A mixture ofthe crude product, Cu2O (1.4 mg, 0.010 mmol), and 1,10-phenanthroline (3.6 mg, 0.020 mmol) in a solution of NMP (1.5mL) and quinoline (0.5 mL) was heated under an atmosphere ofN2 at 170 °C for 24 h. The reaction mixture was quenched byaddition of 0.2 M aq HCl (10 mL), diluted with EtOAc (10 mL),and then filtered through a pad of Celite. The filtrate waswashed with brine (10 mL), dried over Na2SO4, and concentratedin vacuo. The residue was purified by silica gel preparativeTLC to give phenyl(p-tolyl)methanone.

281

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Rx-ID: 41722632

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With palladium(II) trifluoroacetate; silver carbonate in DME

T=150 - 165°C; regioselective reaction; Hide Experimental Procedure

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Pan, Shulei; Zhou, Bo; Zhang, Yanghui; Shao, Changdong; Shi, Guangfa

Synlett, 2016 , vol. 27, # 2 art. no. ST-2015-W0600-L, p. 277 - 281 Title/Abstract Full Text View citing articles Show Details

(20) Synthesis of para-Benzoylated Arenes

General procedure: A mixture of m-toluic acid (27.2 mg, 0.20 mmol), benzoylformicacid (90.1 mg, 0.60 mmol), Pd(TFA)2 (6.6 mg, 0.020 mmol), andAg2CO3 (165.5 mg, 0.60 mmol) in DME (2 mL) was heated at150–165 °C for 24–48 h. After cooling down to r.t., the reactionmixture was diluted by addition of EtOAc (10 mL) and then filteredthrough a pad of Celite. The filtrate was concentrated invacuo to afford 2-benzoylbenzoic acid derivatives. A mixture ofthe crude product, Cu2O (1.4 mg, 0.010 mmol), and 1,10-phenanthroline (3.6 mg, 0.020 mmol) in a solution of NMP (1.5mL) and quinoline (0.5 mL) was heated under an atmosphere ofN2 at 170 °C for 24 h. The reaction mixture was quenched byaddition of 0.2 M aq HCl (10 mL), diluted with EtOAc (10 mL),and then filtered through a pad of Celite. The filtrate waswashed with brine (10 mL), dried over Na2SO4, and concentratedin vacuo. The residue was purified by silica gel preparativeTLC to give phenyl(p-tolyl)methanone.

282

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Rx-ID: 41722638

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With palladium(II) trifluoroacetate; silver carbonate in DME

T=150 - 165°C; regioselective reaction; Hide Experimental Procedure

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Pan, Shulei; Zhou, Bo; Zhang, Yanghui; Shao, Changdong; Shi, Guangfa

Synlett, 2016 , vol. 27, # 2 art. no. ST-2015-W0600-L, p. 277 - 281 Title/Abstract Full Text View citing articles Show Details

(20) Synthesis of para-Benzoylated Arenes

General procedure: A mixture of m-toluic acid (27.2 mg, 0.20 mmol), benzoylformicacid (90.1 mg, 0.60 mmol), Pd(TFA)2 (6.6 mg, 0.020 mmol), andAg2CO3 (165.5 mg, 0.60 mmol) in DME (2 mL) was heated at150–165 °C for 24–48 h. After cooling down to r.t., the reactionmixture was diluted by addition of EtOAc (10 mL) and then filteredthrough a pad of Celite. The filtrate was concentrated invacuo to afford 2-benzoylbenzoic acid derivatives. A mixture ofthe crude product, Cu2O (1.4 mg, 0.010 mmol), and 1,10-phenanthroline (3.6 mg, 0.020 mmol) in a solution of NMP (1.5mL) and quinoline (0.5 mL) was heated under an atmosphere ofN2 at 170 °C for 24 h. The reaction mixture was quenched byaddition of 0.2 M aq HCl (10 mL), diluted with EtOAc (10 mL),and then filtered through a pad of Celite. The filtrate waswashed with brine (10 mL), dried over Na2SO4, and concentratedin vacuo. The residue was purified by silica gel preparativeTLC to give phenyl(p-tolyl)methanone.


283

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Rx-ID: 41722662

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With palladium(II) trifluoroacetate; silver carbonate in DME

T=150 - 165°C; regioselective reaction; Hide Experimental Procedure

Synthesize Find similar

Pan, Shulei; Zhou, Bo; Zhang, Yanghui; Shao, Changdong; Shi, Guangfa

Synlett, 2016 , vol. 27, # 2 art. no. ST-2015-W0600-L, p. 277 - 281 Title/Abstract Full Text View citing articles Show Details

(20) Synthesis of para-Benzoylated Arenes

General procedure: A mixture of m-toluic acid (27.2 mg, 0.20 mmol), benzoylformicacid (90.1 mg, 0.60 mmol), Pd(TFA)2 (6.6 mg, 0.020 mmol), andAg2CO3 (165.5 mg, 0.60 mmol) in DME (2 mL) was heated at150–165 °C for 24–48 h. After cooling down to r.t., the reactionmixture was diluted by addition of EtOAc (10 mL) and then filteredthrough a pad of Celite. The filtrate was concentrated invacuo to afford 2-benzoylbenzoic acid derivatives. A mixture ofthe crude product, Cu2O (1.4 mg, 0.010 mmol), and 1,10-phenanthroline (3.6 mg, 0.020 mmol) in a solution of NMP (1.5mL) and quinoline (0.5 mL) was heated under an atmosphere ofN2 at 170 °C for 24 h. The reaction mixture was quenched byaddition of 0.2 M aq HCl (10 mL), diluted with EtOAc (10 mL),and then filtered through a pad of Celite. The filtrate waswashed with brine (10 mL), dried over Na2SO4, and concentratedin vacuo. The residue was purified by silica gel preparativeTLC to give phenyl(p-tolyl)methanone.

284

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Rx-ID: 43055697

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58%

With water; oxygen in 1,4-dioxane

T=20°C; 48 h; Schlenk techniqueIrradiation;

Xu, Wen-Tao; Huang, Bei; Dai, Jian-Jun; Xu, Jun; Xu, Hua-Jian

Organic Letters, 2016 , vol. 18, # 13 p. 3114 - 3117 Title/Abstract Full Text View citing articles Show Details

40%

With silver trifluoromethanesulfonate in water; acetonitrile

T=60°C; 24 h; Schlenk technique;

Xu, Xiao-Lan; Xu, Wen-Tao; Wu, Ji-Wei; He, Jian-Bo; Xu, Hua-Jian

Organic and Biomolecular Chemistry, 2016 , vol. 14, # 42 p. 9970 - 9973 Title/Abstract Full Text Show Details

285

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Synthesize

Synthesize


Find similar Rx-ID: 43529796

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76%

With potassium pyrosulfate; palladium dichloride in 1,2dichloro-ethane

T=80°C; 24 h; regioselective reaction;

Find similar

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Chen, Xiaopei; Cui, Xiuling; Wu, Yangjie

Organic Letters, 2016 , vol. 18, # 15 p. 3722 - 3725 Title/Abstract Full Text View citing articles Show Details

286

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Rx-ID: 43529806

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76%

With potassium pyrosulfate; palladium dichloride in 1,2dichloro-ethane

T=140°C; 24 h; regioselective reaction;

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Chen, Xiaopei; Cui, Xiuling; Wu, Yangjie

Organic Letters, 2016 , vol. 18, # 15 p. 3722 - 3725 Title/Abstract Full Text View citing articles Show Details

287

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Rx-ID: 728394

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Kharasch; Brown

Journal of the American Chemical Society, 1942 , vol. 64, p. 329,332 Full Text Show Details

6 h; Heating;

Boulmedais, Ali; Jubault, Michel; Tallec, Andre

Bulletin de la Societe Chimique de France, 1988 , # 4 p. 610 - 617 Title/Abstract Full Text Show Details

With N-methyl-acetamide in dichloromethane

Vertex Pharmaceuticals, Inc.

Patent: US5192773 A1, 1993 ;

Hide Experimental Procedure

Title/Abstract Full Text Show Details

1:(S)-N-(Phenylglyoxyl)pipecolic Acid (16)

To this mixture was added 17.72 mmol of benzoylformyl chloride, which was freshly prepared in a separate reaction flasko at ambient temperature from 2.66 g (17.72 mmol) of benzoylformic acid and 2.3 mL (26.37 mmol) of oxalyl chloride in 18.0 mL of methylene chloride containing a catalytic amount of dimethylformamide.


288

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Rx-ID: 728396

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94%

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With dmap; dicyclohexyl-carbodiimide in dichloromethane

T=20°C; Inert atmosphereCooling with ice;

With sulfuric acid; toluene

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Li, Shengkun; Xiao, Taifeng; Li, Dangdang; Zhang, Xumu

Organic Letters, 2015 , vol. 17, # 15 p. 3782 - 3785 Title/Abstract Full Text View citing articles Show Details

Simon

Annales de Chimie (Cachan, France), 1896 , vol. <7> 9, p. 490 Full Text Show Details

Glazer; Turner

Journal of the Chemical Society, 1949 , p. Spl. 169, 173, 175, 176 Full Text Show Details

Hide Details

With hydrochlorid acid

With Hydrogen ion

289

Simon

Annales de Chimie (Cachan, France), 1896 , vol. <7> 9, p. 490 Full Text Show Details

Claisen

Chemische Berichte, 1879 , vol. 12, p. 633 Chemische Berichte, 1877 , vol. 10, p. 1663 Full Text Show Details

Dao, Duc Hai; Okamura, Mutsuo; Akasaka, Takeshi; Kawai, Yasushi; Hida, Kouichi; Ohno, Atsuyoshi

Tetrahedron Asymmetry, 1998 , vol. 9, # 15 p. 2725 - 2737 Title/Abstract Full Text View citing articles Show Details

With thionyl chloride

T=-10 - 20°C; Esterification; 0.5 h;

Kayser, Margaret M.; Mihovilovic, Marko D.; Kearns, Jeff; Feicht, Anton; Stewart, Jon D.

Journal of Organic Chemistry, 1999 , vol. 64, # 18 p. 6603 - 6608 Title/Abstract Full Text View citing articles Show Details

With dmap; dicyclohexyl-carbodiimide in dichloromethane

T=0 - 20°C; 16.0833 h; Inert atmosphere;

Nicolle, Simon M.; Hayes, Christopher J.; Moody, Christopher J.

Chemistry - A European Journal, 2015 , vol. 21, # 12 p. 4576 - 4579 Title/Abstract Full Text View citing articles Show Details


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Rx-ID: 1460215

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100%

With sulfur in benzene

T=80°C; 0.166667 h;

Aly, Moustafa F.; Grigg, Ronald

Tetrahedron, 1988 , vol. 44, # 23 p. 7271 - 7282 Title/Abstract Full Text View citing articles Show Details

100%

With sulfur in benzene

0.166667 h; Heating;

Aly, Moustafa F.; Grigg, Ronald

Journal of the Chemical Society, Chemical Communications, 1985 , # 21 p. 1523 - 1524 Title/Abstract Full Text View citing articles Show Details

290

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Rx-ID: 1485763

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100%

With sulfur in benzene

T=80°C; 0.75 h;

Aly, Moustafa F.; Grigg, Ronald

Tetrahedron, 1988 , vol. 44, # 23 p. 7271 - 7282 Title/Abstract Full Text View citing articles Show Details

With sulfur in benzene

T=80°C; 1 h;

Aly, Moustafa F.; Grigg, Ronald

Journal of the Chemical Society, Chemical Communications, 1985 , # 21 p. 1523 - 1524 Title/Abstract Full Text View citing articles Show Details

291

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Rx-ID: 1561468

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100%

With NH4S2O8; sulfuric acid; silver nitrate in dichloromethane; water

T=40°C; 2.5 h;

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Fontana, Francesca; Minisci, Francesco; Barbosa, Maria Claudia Nogueira; Vismara, Elena

Journal of Organic Chemistry, 1991 , vol. 56, # 8 p. 2866 - 2869 Title/Abstract Full Text View citing articles Show Details


292

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Rx-ID: 1572575

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100%

With NH4S2O8; sulfuric acid; silver nitrate in dichloromethane; water

T=40°C; 2.5 h;

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Fontana, Francesca; Minisci, Francesco; Barbosa, Maria Claudia Nogueira; Vismara, Elena

Journal of Organic Chemistry, 1991 , vol. 56, # 8 p. 2866 - 2869 Title/Abstract Full Text View citing articles Show Details

293

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Rx-ID: 1654645

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100%

With sulfur in benzene

T=80°C; 0.25 h;

Aly, Moustafa F.; Grigg, Ronald

Tetrahedron, 1988 , vol. 44, # 23 p. 7271 - 7282 Title/Abstract Full Text View citing articles Show Details

With sulfur in benzene

T=80°C; 0.25 h;

Aly, Moustafa F.; Grigg, Ronald

Journal of the Chemical Society, Chemical Communications, 1985 , # 21 p. 1523 - 1524 Title/Abstract Full Text View citing articles Show Details

294

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Rx-ID: 4633126

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90%

With 4-(N,N-dimethlyamino)pyridine; dicyclohexylcarbodiimide in dichloromethane

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Hu, Shengkui; Neckers, Douglas C.

Tetrahedron, 1997 , vol. 53, # 8 p. 2751 - 2766


T=0 - 20°C;

Title/Abstract Full Text Show Details

With 4-(N,N-dimethlyamino)pyridine; dicyclohexylcarbodiimide in dichloromethane

T=0°C; Yield given;

Hu, Shengkui; Neckers, Douglas C.

Tetrahedron, 1997 , vol. 53, # 21 p. 7165 - 7180 Title/Abstract Full Text View citing articles Show Details

295

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Rx-ID: 4633132

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92%

With 4-(N,N-dimethlyamino)pyridine; dicyclohexylcarbodiimide in benzene

1.) ice bath, 10 min, 2.) room tenperature, 8 h.;

Hu, Shengkui; Neckers, Douglas C.

Journal of Organic Chemistry, 1996 , vol. 61, # 18 p. 6407 - 6415 Title/Abstract Full Text View citing articles Show Details

With 4-(N,N-dimethlyamino)pyridine; dicyclohexylcarbodiimide in benzene

T=20°C; 12 h; Inert atmosphere;

Martin, Nolwenn J. A.; Cheng, Xu; List, Benjamin

Journal of the American Chemical Society, 2008 , vol. 130, # 42 p. 13862 - 13863 Title/Abstract Full Text View citing articles Show Details

With pyridine in dichloromethane

T=0°C; 1 h;

Weng, Jian-Quan; Deng, Qiao-Man; Wu, Liang; Xu, Kai; Wu, Hao; Liu, Ren-Rong; Gao, Jian-Rong; Jia, Yi-Xia

Organic Letters, 2014 , vol. 16, # 3 p. 776 - 779 Title/Abstract Full Text View citing articles Show Details

296

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Rx-ID: 9021775

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86%

With indium in tetrahydrofuran; water

T=30°C;

Kumar, Subodh; Kaur, Pervinder; Chimni, Swapandeep Singh

Synlett, 2002 , # 4 p. 573 - 574 Title/Abstract Full Text View citing articles Show Details

86%

With indium in tetrahydrofuran; water

T=0°C;

Kaur, Pervinder; Singh, Palwinder; Kumar, Subodh

Tetrahedron, 2005 , vol. 61, # 34 p. 8231 - 8240 Title/Abstract Full Text View citing articles Show Details


297

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Rx-ID: 28501254

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91%

With iodine in water

T=20°C; 10 h;

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Cho, Chia-Ching; Liu, Jia-Nan; Chien, Chung-Hsun; Shie, Jiun-Jie; Chen, Ying-Chu; Fang, Jim-Min

Journal of Organic Chemistry, 2009 , vol. 74, # 4 p. 1549 - 1556 Title/Abstract Full Text View citing articles Show Details


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