Query Query G* N
N
Date
44 reactions in Reaxys
2016-03-23 07h:48m:34s (EST)
G*
O
1. Query
Results G*
G*
NH
NH
Search as: As drawn, No salts, No mixtures
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
1/19
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N
N O
NH
N H
Rx-ID: 187377 View in Reaxys 1/44 Yield
Conditions & References
76 %
With lithium aluminium tetrahydride in tetrahydrofuran, dichloromethane, Time= 48h, Ambient temperature Sintas, Jose A.; Vitale, Arturo A.; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 39; nb. 8; (1997); p. 677 - 684 View in Reaxys
46 %
With lithium aluminium tetrahydride in 1,4-dioxane, T= 100 °C Celik, Leyla; Sinning, Steffen; Severinsen, Kasper; Hansen, Carsten G.; Moller, Maria S.; Bols, Mikael; Wiborg, Ove; Schiott, Birgit; Journal of the American Chemical Society; vol. 130; nb. 12; (2008); p. 3853 - 3865 View in Reaxys With lithium aluminium tetrahydride Fish et al.; Journal of the American Chemical Society; vol. 78; (1956); p. 3668,3670 View in Reaxys
O N
N N H
O N
O
N
NH HN
HN
O
Rx-ID: 41018363 View in Reaxys 2/44 Yield
Conditions & References
87 %
With lithium aluminium tetrahydride in tetrahydrofuran, T= 40 °C , Inert atmosphere, Reflux Stucchi, Mattia; Gmeiner, Peter; Huebner, Harald; Rainoldi, Giulia; Sacchetti, Alessandro; Silvani, Alessandra; Lesma, Giordano; ACS Medicinal Chemistry Letters; vol. 6; nb. 8; (2015); p. 882 - 887 View in Reaxys
O N
N N H
O N
Br
N
NH HN
HN
Br
Rx-ID: 41018365 View in Reaxys 3/44 Yield
Conditions & References
88 %
With lithium aluminium tetrahydride in tetrahydrofuran, T= 40 °C , Inert atmosphere, Reflux Stucchi, Mattia; Gmeiner, Peter; Huebner, Harald; Rainoldi, Giulia; Sacchetti, Alessandro; Silvani, Alessandra; Lesma, Giordano; ACS Medicinal Chemistry Letters; vol. 6; nb. 8; (2015); p. 882 - 887 View in Reaxys
N
N O
O
NH
N H
Rx-ID: 12337198 View in Reaxys 4/44
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
2/19
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Yield
Conditions & References Reaction Steps: 4 1: 71 percent / Cp2ZrCl2 / diethyl ether; tetrahydrofuran / 1 h / 20 °C 2: LiAlH4 / diethyl ether / 20 °C 3: 250 mg / Et3N / CH2Cl2 / 13 h / 0 - 20 °C 4: 91 percent / Grubbs' first generation catalyst / CH2Cl2 / 20 h / 20 °C With lithium aluminium tetrahydride, triethylamine, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys Reaction Steps: 4 1: 926 mg / Cp2ZrCl2 / tetrahydrofuran; diethyl ether / 1 h / 20 °C 2: 87 percent / LiAlH4 / diethyl ether / 20 °C 3: 73 percent / Et3N / CH2Cl2 / 20 °C 4: 91 percent / [RuCl2(PCy3)2CHPh] / CH2Cl2 / 20 °C With lithium aluminium tetrahydride, triethylamine, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Martin, Stephen F; Organic letters; vol. 4; nb. 19; (2002); p. 3243 - 3245 View in Reaxys
N
N O
O
NH
N H
Rx-ID: 12337200 View in Reaxys 5/44 Yield
Conditions & References Reaction Steps: 3 1: 71 percent / Cp2ZrCl2 / diethyl ether; tetrahydrofuran / 1 h / 20 °C 2: LiAlH4 / diethyl ether / 20 °C 3: 250 mg / Et3N / CH2Cl2 / 13 h / 0 - 20 °C With lithium aluminium tetrahydride, triethylamine, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys Reaction Steps: 3 1: 926 mg / Cp2ZrCl2 / tetrahydrofuran; diethyl ether / 1 h / 20 °C 2: 87 percent / LiAlH4 / diethyl ether / 20 °C 3: 73 percent / Et3N / CH2Cl2 / 20 °C With lithium aluminium tetrahydride, triethylamine, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Martin, Stephen F; Organic letters; vol. 4; nb. 19; (2002); p. 3243 - 3245 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
3/19
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N
N O
O
NH
N H
Rx-ID: 12337269 View in Reaxys 6/44 Yield
Conditions & References Reaction Steps: 5 1: Grubbs' first generation catalyst / tetrahydrofuran / 29 h / 20 °C 2: 71 percent / Cp2ZrCl2 / diethyl ether; tetrahydrofuran / 1 h / 20 °C 3: LiAlH4 / diethyl ether / 20 °C 4: 250 mg / Et3N / CH2Cl2 / 13 h / 0 - 20 °C 5: 91 percent / Grubbs' first generation catalyst / CH2Cl2 / 20 h / 20 °C With lithium aluminium tetrahydride, triethylamine, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys Reaction Steps: 5 1: [(C6H11)3P]2Cl2RuC2H3Ph / tetrahydrofuran / 29 h / 20 °C 2: 926 mg / Cp2ZrCl2 / tetrahydrofuran; diethyl ether / 1 h / 20 °C 3: 87 percent / LiAlH4 / diethyl ether / 20 °C 4: 73 percent / Et3N / CH2Cl2 / 20 °C 5: 91 percent / [RuCl2(PCy3)2CHPh] / CH2Cl2 / 20 °C With lithium aluminium tetrahydride, triethylamine, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Martin, Stephen F; Organic letters; vol. 4; nb. 19; (2002); p. 3243 - 3245 View in Reaxys
N
N
O
O N H
NH
Rx-ID: 12337272 View in Reaxys 7/44 Yield
Conditions & References Reaction Steps: 4 1: Grubbs' first generation catalyst / tetrahydrofuran / 29 h / 20 °C 2: 71 percent / Cp2ZrCl2 / diethyl ether; tetrahydrofuran / 1 h / 20 °C 3: LiAlH4 / diethyl ether / 20 °C 4: 250 mg / Et3N / CH2Cl2 / 13 h / 0 - 20 °C With lithium aluminium tetrahydride, triethylamine, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys Reaction Steps: 4 1: [(C6H11)3P]2Cl2RuC2H3Ph / tetrahydrofuran / 29 h / 20 °C 2: 926 mg / Cp2ZrCl2 / tetrahydrofuran; diethyl ether / 1 h / 20 °C 3: 87 percent / LiAlH4 / diethyl ether / 20 °C
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
4/19
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4: 73 percent / Et3N / CH2Cl2 / 20 °C With lithium aluminium tetrahydride, triethylamine, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Martin, Stephen F; Organic letters; vol. 4; nb. 19; (2002); p. 3243 - 3245 View in Reaxys
N
N O
O
NH
NH
Rx-ID: 14669526 View in Reaxys 8/44 Yield
Conditions & References Reaction Steps: 5 1: 926 mg / Cp2ZrCl2 / tetrahydrofuran; diethyl ether / 1 h / 20 °C 2: 87 percent / LiAlH4 / diethyl ether / 20 °C 3: 73 percent / Et3N / CH2Cl2 / 20 °C 4: 91 percent / [RuCl2(PCy3)2CHPh] / CH2Cl2 / 20 °C 5: 91 percent / CuCN; TMSCl / tetrahydrofuran / -78 - 20 °C With lithium aluminium tetrahydride, chloro-trimethyl-silane, triethylamine, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Martin, Stephen F; Organic letters; vol. 4; nb. 19; (2002); p. 3243 - 3245 View in Reaxys
N
N O O
NH
NH
Rx-ID: 14671872 View in Reaxys 9/44 Yield
Conditions & References Reaction Steps: 6 1: [(C6H11)3P]2Cl2RuC2H3Ph / tetrahydrofuran / 29 h / 20 °C 2: 926 mg / Cp2ZrCl2 / tetrahydrofuran; diethyl ether / 1 h / 20 °C 3: 87 percent / LiAlH4 / diethyl ether / 20 °C 4: 73 percent / Et3N / CH2Cl2 / 20 °C 5: 91 percent / [RuCl2(PCy3)2CHPh] / CH2Cl2 / 20 °C 6: 91 percent / CuCN; TMSCl / tetrahydrofuran / -78 - 20 °C With lithium aluminium tetrahydride, chloro-trimethyl-silane, triethylamine, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Martin, Stephen F; Organic letters; vol. 4; nb. 19; (2002); p. 3243 - 3245 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
5/19
2016-03-23 07:56:31
N
N
O
NH
NH
Rx-ID: 35987962 View in Reaxys 10/44 Yield
Conditions & References
96 %
With lithium aluminium tetrahydride in tetrahydrofuran, Time= 4h, Inert atmosphere, Reflux Ghislieri, Diego; Green, Anthony P.; Pontini, Marta; Willies, Simon C.; Rowles, Ian; Frank, Annika; Grogan, Gideon; Turner, Nicholas J.; Journal of the American Chemical Society; vol. 135; nb. 29; (2013); p. 10863 - 10869 View in Reaxys
N
N O
O
NH
NH
Rx-ID: 12337183 View in Reaxys 11/44 Yield
Conditions & References Reaction Steps: 5 1.1: 71 percent / Cp2ZrCl2 / diethyl ether; tetrahydrofuran / 1 h / 20 °C 2.1: LiAlH4 / diethyl ether / 20 °C 3.1: 250 mg / Et3N / CH2Cl2 / 13 h / 0 - 20 °C 4.1: 91 percent / Grubbs' first generation catalyst / CH2Cl2 / 20 h / 20 °C 5.1: CuCN / tetrahydrofuran / -78 - 0 °C 5.2: 16 percent / tetrahydrofuran / 3.25 h / -78 - 20 °C With lithium aluminium tetrahydride, triethylamine, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys
N
N O
O
NH
NH
Rx-ID: 12337184 View in Reaxys 12/44 Yield
Conditions & References Reaction Steps: 5 1.1: 71 percent / Cp2ZrCl2 / diethyl ether; tetrahydrofuran / 1 h / 20 °C 2.1: LiAlH4 / diethyl ether / 20 °C 3.1: 250 mg / Et3N / CH2Cl2 / 13 h / 0 - 20 °C 4.1: 91 percent / Grubbs' first generation catalyst / CH2Cl2 / 20 h / 20 °C 5.1: CuBr*DMS / tetrahydrofuran / -78 - 0 °C 5.2: TMSCl / tetrahydrofuran / 3.75 h / -78 - 20 °C With lithium aluminium tetrahydride, copper(I) bromide dimethylsulfide complex, triethylamine, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
6/19
2016-03-23 07:56:31
View in Reaxys
N
N O
O
NH
NH racemate
Rx-ID: 12337185 View in Reaxys 13/44 Yield
Conditions & References Reaction Steps: 5 1.1: 71 percent / Cp2ZrCl2 / diethyl ether; tetrahydrofuran / 1 h / 20 °C 2.1: LiAlH4 / diethyl ether / 20 °C 3.1: 250 mg / Et3N / CH2Cl2 / 13 h / 0 - 20 °C 4.1: 91 percent / Grubbs' first generation catalyst / CH2Cl2 / 20 h / 20 °C 5.1: CuCN / tetrahydrofuran / -78 - 0 °C 5.2: 91 percent / TMSCl / tetrahydrofuran / 3.75 h / -78 - 20 °C With lithium aluminium tetrahydride, triethylamine, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys
Si
N
O N O
NH
NH racemate
Rx-ID: 12337191 View in Reaxys 14/44 Yield
Conditions & References Reaction Steps: 5 1.1: 71 percent / Cp2ZrCl2 / diethyl ether; tetrahydrofuran / 1 h / 20 °C 2.1: LiAlH4 / diethyl ether / 20 °C 3.1: 250 mg / Et3N / CH2Cl2 / 13 h / 0 - 20 °C 4.1: 91 percent / Grubbs' first generation catalyst / CH2Cl2 / 20 h / 20 °C 5.1: CuCN / tetrahydrofuran / -78 - 0 °C 5.2: 75 percent / TMSCl / tetrahydrofuran / 3.75 h / -78 - 20 °C With lithium aluminium tetrahydride, triethylamine, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
7/19
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O
S S
O N
O N
O
NH
NH racemate
Rx-ID: 12337192 View in Reaxys 15/44 Yield
Conditions & References Reaction Steps: 5 1.1: 71 percent / Cp2ZrCl2 / diethyl ether; tetrahydrofuran / 1 h / 20 °C 2.1: LiAlH4 / diethyl ether / 20 °C 3.1: 250 mg / Et3N / CH2Cl2 / 13 h / 0 - 20 °C 4.1: 91 percent / Grubbs' first generation catalyst / CH2Cl2 / 20 h / 20 °C 5.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C 5.2: 71 percent / tetrahydrofuran / 20 h / -78 - 20 °C With lithium aluminium tetrahydride, triethylamine, lithium diisopropyl amide, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys
H N
N O
N O
N O
NH
HN
Rx-ID: 12337194 View in Reaxys 16/44 Yield
Conditions & References Reaction Steps: 5 1.1: 71 percent / Cp2ZrCl2 / diethyl ether; tetrahydrofuran / 1 h / 20 °C 2.1: LiAlH4 / diethyl ether / 20 °C 3.1: 250 mg / Et3N / CH2Cl2 / 13 h / 0 - 20 °C 4.1: 91 percent / Grubbs' first generation catalyst / CH2Cl2 / 20 h / 20 °C 5.1: CuCN / tetrahydrofuran / -78 - 0 °C 5.2: 57 percent / tetrahydrofuran / 3.25 h / -78 - 20 °C With lithium aluminium tetrahydride, triethylamine, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
8/19
2016-03-23 07:56:31
N
N O
O
NH
N H
Rx-ID: 12337195 View in Reaxys 17/44 Yield
Conditions & References Reaction Steps: 5 1: 71 percent / Cp2ZrCl2 / diethyl ether; tetrahydrofuran / 1 h / 20 °C 2: LiAlH4 / diethyl ether / 20 °C 3: 250 mg / Et3N / CH2Cl2 / 13 h / 0 - 20 °C 4: 91 percent / Grubbs' first generation catalyst / CH2Cl2 / 20 h / 20 °C 5: H2 / palladium on carbon / toluene / 14 h / 760 Torr With lithium aluminium tetrahydride, hydrogen, triethylamine, palladium on activated charcoal, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane, toluene Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys
N
N O
O
NH
NH
Rx-ID: 12337254 View in Reaxys 18/44 Yield
Conditions & References Reaction Steps: 6 1.1: Grubbs' first generation catalyst / tetrahydrofuran / 29 h / 20 °C 2.1: 71 percent / Cp2ZrCl2 / diethyl ether; tetrahydrofuran / 1 h / 20 °C 3.1: LiAlH4 / diethyl ether / 20 °C 4.1: 250 mg / Et3N / CH2Cl2 / 13 h / 0 - 20 °C 5.1: 91 percent / Grubbs' first generation catalyst / CH2Cl2 / 20 h / 20 °C 6.1: CuCN / tetrahydrofuran / -78 - 0 °C 6.2: 16 percent / tetrahydrofuran / 3.25 h / -78 - 20 °C With lithium aluminium tetrahydride, triethylamine, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys
N
N O
O
NH
NH
Rx-ID: 12337255 View in Reaxys 19/44 Yield
Conditions & References Reaction Steps: 6
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
9/19
2016-03-23 07:56:31
1.1: Grubbs' first generation catalyst / tetrahydrofuran / 29 h / 20 °C 2.1: 71 percent / Cp2ZrCl2 / diethyl ether; tetrahydrofuran / 1 h / 20 °C 3.1: LiAlH4 / diethyl ether / 20 °C 4.1: 250 mg / Et3N / CH2Cl2 / 13 h / 0 - 20 °C 5.1: 91 percent / Grubbs' first generation catalyst / CH2Cl2 / 20 h / 20 °C 6.1: CuBr*DMS / tetrahydrofuran / -78 - 0 °C 6.2: TMSCl / tetrahydrofuran / 3.75 h / -78 - 20 °C With lithium aluminium tetrahydride, copper(I) bromide dimethylsulfide complex, triethylamine, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys
N
N O
O
NH
NH
racemate
Rx-ID: 12337256 View in Reaxys 20/44 Yield
Conditions & References Reaction Steps: 6 1.1: Grubbs' first generation catalyst / tetrahydrofuran / 29 h / 20 °C 2.1: 71 percent / Cp2ZrCl2 / diethyl ether; tetrahydrofuran / 1 h / 20 °C 3.1: LiAlH4 / diethyl ether / 20 °C 4.1: 250 mg / Et3N / CH2Cl2 / 13 h / 0 - 20 °C 5.1: 91 percent / Grubbs' first generation catalyst / CH2Cl2 / 20 h / 20 °C 6.1: CuCN / tetrahydrofuran / -78 - 0 °C 6.2: 91 percent / TMSCl / tetrahydrofuran / 3.75 h / -78 - 20 °C With lithium aluminium tetrahydride, triethylamine, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys
Si
N
O N
O
NH
NH racemate
Rx-ID: 12337262 View in Reaxys 21/44 Yield
Conditions & References Reaction Steps: 6 1.1: Grubbs' first generation catalyst / tetrahydrofuran / 29 h / 20 °C 2.1: 71 percent / Cp2ZrCl2 / diethyl ether; tetrahydrofuran / 1 h / 20 °C 3.1: LiAlH4 / diethyl ether / 20 °C 4.1: 250 mg / Et3N / CH2Cl2 / 13 h / 0 - 20 °C 5.1: 91 percent / Grubbs' first generation catalyst / CH2Cl2 / 20 h / 20 °C 6.1: CuCN / tetrahydrofuran / -78 - 0 °C 6.2: 75 percent / TMSCl / tetrahydrofuran / 3.75 h / -78 - 20 °C
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
10/19
2016-03-23 07:56:31
With lithium aluminium tetrahydride, triethylamine, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys
O
S S
O N
O N O
NH
NH racemate
Rx-ID: 12337263 View in Reaxys 22/44 Yield
Conditions & References Reaction Steps: 6 1.1: Grubbs' first generation catalyst / tetrahydrofuran / 29 h / 20 °C 2.1: 71 percent / Cp2ZrCl2 / diethyl ether; tetrahydrofuran / 1 h / 20 °C 3.1: LiAlH4 / diethyl ether / 20 °C 4.1: 250 mg / Et3N / CH2Cl2 / 13 h / 0 - 20 °C 5.1: 91 percent / Grubbs' first generation catalyst / CH2Cl2 / 20 h / 20 °C 6.1: lithium diisopropyl amide / tetrahydrofuran / 1 h / -78 °C 6.2: 71 percent / tetrahydrofuran / 20 h / -78 - 20 °C With lithium aluminium tetrahydride, triethylamine, lithium diisopropyl amide, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys
H N
N O N O
N O NH
HN
Rx-ID: 12337265 View in Reaxys 23/44 Yield
Conditions & References Reaction Steps: 6 1.1: Grubbs' first generation catalyst / tetrahydrofuran / 29 h / 20 °C 2.1: 71 percent / Cp2ZrCl2 / diethyl ether; tetrahydrofuran / 1 h / 20 °C 3.1: LiAlH4 / diethyl ether / 20 °C 4.1: 250 mg / Et3N / CH2Cl2 / 13 h / 0 - 20 °C 5.1: 91 percent / Grubbs' first generation catalyst / CH2Cl2 / 20 h / 20 °C 6.1: CuCN / tetrahydrofuran / -78 - 0 °C 6.2: 57 percent / tetrahydrofuran / 3.25 h / -78 - 20 °C With lithium aluminium tetrahydride, triethylamine, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
11/19
2016-03-23 07:56:31
Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys
N N O
O
NH
N H
Rx-ID: 12337266 View in Reaxys 24/44 Yield
Conditions & References Reaction Steps: 6 1: Grubbs' first generation catalyst / tetrahydrofuran / 29 h / 20 °C 2: 71 percent / Cp2ZrCl2 / diethyl ether; tetrahydrofuran / 1 h / 20 °C 3: LiAlH4 / diethyl ether / 20 °C 4: 250 mg / Et3N / CH2Cl2 / 13 h / 0 - 20 °C 5: 91 percent / Grubbs' first generation catalyst / CH2Cl2 / 20 h / 20 °C 6: H2 / palladium on carbon / toluene / 14 h / 760 Torr With lithium aluminium tetrahydride, hydrogen, triethylamine, palladium on activated charcoal, bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride, zirconocene dichloride in tetrahydrofuran, diethyl ether, dichloromethane, toluene Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys
O
O
N
N O
HN
HN
Rx-ID: 11066006 View in Reaxys 25/44 Yield
Conditions & References With lithium aluminium tetrahydride in tetrahydrofuran, Time= 2h, T= 0 °C Cheng, Kejun; Kim, In Jong; Lee, Mei-Jing; Adah, Steven A.; Raymond, Tyler J.; Bilsky, Edward J.; Aceto, Mario D.; May, Everette L.; Harris, Louis S.; Coop, Andrew; Dersch, Christina M.; Rothman, Richard B.; Jacobson, Arthur E.; Rice, Kenner C.; Organic and Biomolecular Chemistry; vol. 5; nb. 8; (2007); p. 1177 - 1190 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
12/19
2016-03-23 07:56:31
O
O
N
N
O HN
HN
Rx-ID: 11066008 View in Reaxys 26/44 Yield
Conditions & References With lithium aluminium tetrahydride in tetrahydrofuran, Time= 2h, T= 0 °C Cheng, Kejun; Kim, In Jong; Lee, Mei-Jing; Adah, Steven A.; Raymond, Tyler J.; Bilsky, Edward J.; Aceto, Mario D.; May, Everette L.; Harris, Louis S.; Coop, Andrew; Dersch, Christina M.; Rothman, Richard B.; Jacobson, Arthur E.; Rice, Kenner C.; Organic and Biomolecular Chemistry; vol. 5; nb. 8; (2007); p. 1177 - 1190 View in Reaxys
N
N
O
NH
NH
Rx-ID: 3218239 View in Reaxys 27/44 Yield
Conditions & References With sodium bis(2-methoxyethoxy)aluminium dihydride in tetrahydrofuran, Time= 2h, Ambient temperature Bottcher; Barnickel; Hausberg; Haase; Seyfried; Eiermann; Journal of Medicinal Chemistry; vol. 35; nb. 22; (1992); p. 4020 - 4026 View in Reaxys
F
O
F
N
O
F
NH H N
F N O
Rx-ID: 4848469 View in Reaxys 28/44 Yield
Conditions & References With lithium aluminium tetrahydride, sulfuric acid in tetrahydrofuran, Time= 2h, Ambient temperature, Yield given Agoston, Gregory E.; Wu, Jae H.; Izenwasser, Sari; George, Clifford; Katz, Jonathan; Kline, Richard H.; Newman, Amy Hauck; Journal of Medicinal Chemistry; vol. 40; nb. 26; (1997); p. 4329 - 4339 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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O
Br Z
OH
Br Z
O
N
N O
NH
NH
Rx-ID: 8724135 View in Reaxys 29/44 Yield
Conditions & References With diisobutylaluminium hydride in dichloromethane, T= -78 °C Sakagami, Hideki; Ogasawara, Kunio; Heterocycles; vol. 54; nb. 1; (2001); p. 43 - 47 View in Reaxys
N O
N
N
N O NH
NH
Rx-ID: 18465630 View in Reaxys 30/44 Yield
Conditions & References Reaction Steps: 2 1: LiAlH4 / diethyl ether / 2 h / Heating 2: 1.) trifluoroacetic anhydride, 2.) 15percent aq. NaOH / 1.) CH2Cl2, r.t., 4 h, 2.) MeOH, r.t., 6 h With sodium hydroxide, lithium aluminium tetrahydride, trifluoroacetic anhydride in diethyl ether Mangeney; Gosmini; Raussou; Commercon; Alexakis; Journal of Organic Chemistry; vol. 59; nb. 7; (1994); p. 1877 - 1888 View in Reaxys
NH N
N N N
N N
N N
O
N
NH
NH
Rx-ID: 3694059 View in Reaxys 31/44 Yield
Conditions & References With lithium aluminium tetrahydride in diethyl ether, Time= 2h, Heating, Yield given. Yields of byproduct given. Title compound not separated from byproducts Mangeney; Gosmini; Raussou; Commercon; Alexakis; Journal of Organic Chemistry; vol. 59; nb. 7; (1994); p. 1877 - 1888 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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OH
O
N
N O HN
HN
Rx-ID: 11597807 View in Reaxys 32/44 Yield
Conditions & References Reaction Steps: 2 1: LiAlH4 / tetrahydrofuran / 2 h / 0 °C 2: BBr3*SMe2 / CH2Cl2; 1,2-dichloro-ethane / Heating With lithium aluminium tetrahydride, BBr3*Me2S complex in tetrahydrofuran, dichloromethane, 1,2-dichloro-ethane Cheng, Kejun; Kim, In Jong; Lee, Mei-Jing; Adah, Steven A.; Raymond, Tyler J.; Bilsky, Edward J.; Aceto, Mario D.; May, Everette L.; Harris, Louis S.; Coop, Andrew; Dersch, Christina M.; Rothman, Richard B.; Jacobson, Arthur E.; Rice, Kenner C.; Organic and Biomolecular Chemistry; vol. 5; nb. 8; (2007); p. 1177 - 1190 View in Reaxys
OH
O
N
N O HN
HN
Rx-ID: 11597808 View in Reaxys 33/44 Yield
Conditions & References Reaction Steps: 2 1: LiAlH4 / tetrahydrofuran / 2 h / 0 °C 2: BBr3*SMe2 / CH2Cl2; 1,2-dichloro-ethane / Heating With lithium aluminium tetrahydride, BBr3*Me2S complex in tetrahydrofuran, dichloromethane, 1,2-dichloro-ethane Cheng, Kejun; Kim, In Jong; Lee, Mei-Jing; Adah, Steven A.; Raymond, Tyler J.; Bilsky, Edward J.; Aceto, Mario D.; May, Everette L.; Harris, Louis S.; Coop, Andrew; Dersch, Christina M.; Rothman, Richard B.; Jacobson, Arthur E.; Rice, Kenner C.; Organic and Biomolecular Chemistry; vol. 5; nb. 8; (2007); p. 1177 - 1190 View in Reaxys
N
O N H
N
N
O N
O
N
NH
O
HN
Rx-ID: 41018364 View in Reaxys 34/44 Yield
Conditions & References Reaction Steps: 2 1: lithium aluminium tetrahydride / tetrahydrofuran / 40 °C / |Inert atmosphere; |Reflux 2: sodium tris(acetoxy)borohydride / dichloromethane / 20 °C With lithium aluminium tetrahydride, sodium tris(acetoxy)borohydride in tetrahydrofuran, dichloromethane
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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Stucchi, Mattia; Gmeiner, Peter; Huebner, Harald; Rainoldi, Giulia; Sacchetti, Alessandro; Silvani, Alessandra; Lesma, Giordano; ACS Medicinal Chemistry Letters; vol. 6; nb. 8; (2015); p. 882 - 887 View in Reaxys
N
O N H
N
N
O N
Br
N
NH
Br
HN
Rx-ID: 41018366 View in Reaxys 35/44 Yield
Conditions & References Reaction Steps: 2 1: lithium aluminium tetrahydride / tetrahydrofuran / 40 °C / |Inert atmosphere; |Reflux 2: sodium tris(acetoxy)borohydride / dichloromethane / 20 °C With lithium aluminium tetrahydride, sodium tris(acetoxy)borohydride in tetrahydrofuran, dichloromethane Stucchi, Mattia; Gmeiner, Peter; Huebner, Harald; Rainoldi, Giulia; Sacchetti, Alessandro; Silvani, Alessandra; Lesma, Giordano; ACS Medicinal Chemistry Letters; vol. 6; nb. 8; (2015); p. 882 - 887 View in Reaxys
N
N
N
N
N
N
O
NH
NH
Rx-ID: 2763721 View in Reaxys 36/44 Yield
Conditions & References With lithium aluminium tetrahydride in diethyl ether, Time= 12h, Heating Mangeney, Pierre; Gosmini, Romain; Alexakis, Alexandre; Tetrahedron Letters; vol. 32; nb. 32; (1991); p. 3981 3984 View in Reaxys
N
N N
N
N
N
O
N H
NH
Rx-ID: 2992670 View in Reaxys 37/44 Yield
Conditions & References With lithium aluminium tetrahydride in tetrahydrofuran, Time= 3h, Heating Golubev, V. E.; Trubitsyna, T. K.; Mashkovskii, M. D.; Suvorov, N. N.; Pharmaceutical Chemistry Journal; vol. 15; nb. 2; (1981); p. 88 - 90; Khimiko-Farmatsevticheskii Zhurnal; vol. 15; nb. 2; (1981); p. 30 - 33 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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OH
Br
O
Z
N
N O
NH
NH
Rx-ID: 15700722 View in Reaxys 38/44 Yield
Conditions & References Reaction Steps: 2 1: CH2Cl2 / 20 °C 2: diisobutylaluminum hydride / CH2Cl2 / -78 °C With diisobutylaluminium hydride in dichloromethane, 1: Wittig reaction Sakagami, Hideki; Ogasawara, Kunio; Heterocycles; vol. 54; nb. 1; (2001); p. 43 - 47 View in Reaxys
O O
O
Br Z
N
N O
NH
NH
Rx-ID: 15700723 View in Reaxys 39/44 Yield
Conditions & References Reaction Steps: 3 1: CH2Cl2 / 20 °C 2: diisobutylaluminum hydride / CH2Cl2 / -78 °C 3: pyridine With pyridine, diisobutylaluminium hydride in dichloromethane, 1: Wittig reaction Sakagami, Hideki; Ogasawara, Kunio; Heterocycles; vol. 54; nb. 1; (2001); p. 43 - 47 View in Reaxys
OH
Br
O
Z
N
N
O
NH NH
Rx-ID: 15700855 View in Reaxys 40/44 Yield
Conditions & References Reaction Steps: 3 1: Amberlyst-15 / acetone; H2O 2: CH2Cl2 / 20 °C 3: diisobutylaluminum hydride / CH2Cl2 / -78 °C With amberlyst-15, diisobutylaluminium hydride in dichloromethane, water, acetone, 2: Wittig reaction Sakagami, Hideki; Ogasawara, Kunio; Heterocycles; vol. 54; nb. 1; (2001); p. 43 - 47
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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View in Reaxys
O O
O
Br Z
N
N O
NH
NH
Rx-ID: 15700857 View in Reaxys 41/44 Yield
Conditions & References Reaction Steps: 4 1: Amberlyst-15 / acetone; H2O 2: CH2Cl2 / 20 °C 3: diisobutylaluminum hydride / CH2Cl2 / -78 °C 4: pyridine With pyridine, amberlyst-15, diisobutylaluminium hydride in dichloromethane, water, acetone, 2: Wittig reaction Sakagami, Hideki; Ogasawara, Kunio; Heterocycles; vol. 54; nb. 1; (2001); p. 43 - 47 View in Reaxys
O
O
Br
O
Br
Z
O
Z
N
N
O
NH
NH
Rx-ID: 15704332 View in Reaxys 42/44 Yield
Conditions & References Reaction Steps: 2 1: diisobutylaluminum hydride / CH2Cl2 / -78 °C 2: pyridine With pyridine, diisobutylaluminium hydride in dichloromethane Sakagami, Hideki; Ogasawara, Kunio; Heterocycles; vol. 54; nb. 1; (2001); p. 43 - 47 View in Reaxys
N
N
O
NH
NH
Rx-ID: 10333074 View in Reaxys 43/44 Yield
Conditions & References With lithium aluminium tetrahydride Deiters, Alexander; Pettersson, Martin; Martin, Stephen F.; Journal of Organic Chemistry; vol. 71; nb. 17; (2006); p. 6547 - 6561 View in Reaxys
Copyright © 2016 Reed Elsevier Properties SA. All rights reserved. Authorized use only. Reaxys® and the Reaxys® trademark are owned and protected by Reed Elsevier Properties SA and used under license.
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F
NH
F
F
NH
F
N
N
O HN
HN
Rx-ID: 10010626 View in Reaxys 44/44 Yield
Conditions & References With lithium aluminium tetrahydride Grundt, Peter; Kopajtic, Theresa A.; Katz, Jonathan L.; Newman, Amy Hauck; Bioorganic and Medicinal Chemistry Letters; vol. 15; nb. 24; (2005); p. 5419 - 5423 View in Reaxys
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19/19
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