Query Query G*
HN
HN
O
O
1. Query NH
Results
Date
14 reactions in Reaxys
2016-03-23 08h:46m:46s (EST)
G*
NH
Search as: As drawn, No salts, No mixtures
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NH O N
HN
O
O
O
HN
O
O
O
O
OH
O
NH HN
Rx-ID: 9083679 View in Reaxys 1/14 Yield
Conditions & References With diethylphosphinoethane, tris(dibenzylideneacetone)dipalladium(0) chloroform complex in tetrahydrofuran, Time= 16h, T= 20 °C
92 %
Trost, Barry M; Krische, Michael J; Berl, Volker; Grenzer, Ellen M; Organic letters; vol. 4; nb. 12; (2002); p. 2005 - 2008 View in Reaxys
NH O O
HN
O
N
O HN
O
O
O
OH
O O
O
O O
NH
HN
O
O
O
Rx-ID: 9083680 View in Reaxys 2/14 Yield
Conditions & References With diethylphosphinoethane, tris(dibenzylideneacetone)dipalladium(0) chloroform complex in tetrahydrofuran, Time= 16h, T= 20 °C
96 %
Trost, Barry M; Krische, Michael J; Berl, Volker; Grenzer, Ellen M; Organic letters; vol. 4; nb. 12; (2002); p. 2005 - 2008 View in Reaxys
HN
O
HN
O
NH
N H
Rx-ID: 39059092 View in Reaxys 3/14 Yield
Conditions & References General procedure: To a solution of 4’-Fluoro-2,3-di-oxotryptamine (3b, 644 mg, 3.12 mmol) in THF (30 mL), a 1.0 M LiAlH4/THF solution (16 mL, 16 mmol) was added slowly and the mixture was refluxed for 18 h. The reaction was quenched with water/THF (1/1) and made basic (pH 10) with 3 N aqueous NaOH. The solids were filtered through Celite; the filtrate was dried with anhydrous MgSO4and concentrated. The crude material was purified by automated flash chromatography (silica gel, 20percent MeOH/DCM) to obtain 130 mg of colorless oil (23percent). This material was dissolved in diethyl ether (100 mL) and MeOH (1 mL) and a solution of Fumaric Acid (90 mg, 0.77 mmol) in MeOH (9 mL) was added. The reaction stirred at room temperature for 60 h and the resulting solids were filtered, washed with ether and dried. The dry solids were recrystallized (MeOH/ethyl acetate) to yield 70.3 mg of product With lithium aluminium tetrahydride in tetrahydrofuran, Time= 18h, Reflux Blough, Bruce E.; Landavazo, Antonio; Decker, Ann M.; Page, Kevin M.; Partilla, John S.; Baumann, Michael H.; Rothman, Richard B.; Bioorg. Med. Chem. Lett.; vol. 24; nb. 19; (2014); p. 4754 - 4758 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.
2/6
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HN
O
HO
HN HO
O
NH NH
racemate
Rx-ID: 5302428 View in Reaxys 4/14 Yield
Conditions & References
49 %
With lithium aluminium tetrahydride in tetrahydrofuran, Time= 5h, T= 20 °C , Reduction Hashem, Md. Abul; Sultana, Israt; Hai, Abdul; Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry; vol. 38; nb. 7; (1999); p. 789 - 794 View in Reaxys
HN
NH O
O HN
NH
Rx-ID: 5172103 View in Reaxys 5/14 Yield
Conditions & References
96 %
With lithium aluminium tetrahydride, aluminium trichloride in tetrahydrofuran, 2 h, 0 deg C; 5 h, RT Kawate, Tomohiko; Yamanaka, Masamichi; Nakagawa, Masako; Heterocycles; vol. 50; nb. 2; (1999); p. 1033 1039 View in Reaxys
NH HO NH
HN
O
HN O
O
NH
HN
Rx-ID: 3098205 View in Reaxys 6/14 Yield 80 %
Conditions & References With sodium tetrahydroborate in ethanol, Time= 2.5h, Ambient temperature da Settimo; Primofiore; Marini; Mori; Franzone; Cirillo; Reboani; Farmaco, Edizione Scientifica; vol. 42; nb. 1; (1987); p. 17 - 26 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.
3/6
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HN
NH O
O HN
NH
Rx-ID: 5172104 View in Reaxys 7/14 Yield
Conditions & References
84 %
With lithium aluminium tetrahydride, aluminium trichloride in tetrahydrofuran, 2 h, 0 deg C; 5 h, RT Kawate, Tomohiko; Yamanaka, Masamichi; Nakagawa, Masako; Heterocycles; vol. 50; nb. 2; (1999); p. 1033 1039 View in Reaxys
NH O
O
N
HN
O
O
N HN
O
O
O O
HN
NH
HN
NH
Rx-ID: 9062085 View in Reaxys 8/14 Yield
Conditions & References With tris(dibenzylideneacetone)dipalladium(0) chloroform complex, S,S-DACHN, caesium carbonate in tetrahydrofuran, Time= 12h, T= 50 °C , Title compound not separated from byproducts. Trost, Barry M; Krische, Michael J; Berl, Volker; Grenzer, Ellen M; Organic letters; vol. 4; nb. 12; (2002); p. 2005 - 2008 View in Reaxys
HN
O
HN O
NH
NH
Rx-ID: 4367246 View in Reaxys 9/14 Yield
Conditions & References
62 %
With lithium aluminium tetrahydride, aluminium trichloride in tetrahydrofuran, 0 degC, 1 h then room t., overnight Soe, Than; Kawate, Tomohiko; Fukui, Naoko; Hino, Tohru; Nakagawa, Masako; Heterocycles; vol. 42; nb. 1; (1996); p. 347 - 358 View in Reaxys
HN
O
NH
HN NH O
NH
OH NH HN
HN
Rx-ID: 4986318 View in Reaxys 10/14
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Yield
Conditions & References
36 %, 24 %, 29 %
With dimethylsulfide borane complex in tetrahydrofuran, Time= 48h, Heating Burm, Brigitte E.A.; Meijler, Michael M.; Korver, Jacco; Wanner, Martin J.; Koomen, Gerrit-Jan; Tetrahedron; vol. 54; nb. 22; (1998); p. 6135 - 6146 View in Reaxys
29 %, 36 %, 24 %
With dimethylsulfide borane complex in tetrahydrofuran, Time= 48h, Heating Burm, Brigitte E.A.; Meijler, Michael M.; Korver, Jacco; Wanner, Martin J.; Koomen, Gerrit-Jan; Tetrahedron; vol. 54; nb. 22; (1998); p. 6135 - 6146 View in Reaxys
29 %, 24 %, 36 %
With dimethylsulfide borane complex in tetrahydrofuran, Time= 48h, Heating Burm, Brigitte E.A.; Meijler, Michael M.; Korver, Jacco; Wanner, Martin J.; Koomen, Gerrit-Jan; Tetrahedron; vol. 54; nb. 22; (1998); p. 6135 - 6146 View in Reaxys
Cl
Cl HN
HN
O
O
N H
NH
Rx-ID: 2592865 View in Reaxys 11/14 Yield
Conditions & References
50 %
With lithium aluminium tetrahydride in diethyl ether, Time= 12h, Heating Kumar; Agarwal; Nath; et al.; Journal of Heterocyclic Chemistry; vol. 18; nb. 6; (1981); p. 1269 - 1271 View in Reaxys
HN
O
HN
O N H
NH
Rx-ID: 2589084 View in Reaxys 12/14 Yield
Conditions & References
30 %
With lithium aluminium tetrahydride in diethyl ether, Time= 12h, Heating Kumar; Agarwal; Nath; et al.; Journal of Heterocyclic Chemistry; vol. 18; nb. 6; (1981); p. 1269 - 1271 View in Reaxys
HN
O
HN O
NH
NH
Rx-ID: 371249 View in Reaxys 13/14 Yield
Conditions & References With lithium aluminium tetrahydride Patent; Upjohn Co.; US2870162; (1954) 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.
5/6
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O
HN
HN
O
N H
NH
Rx-ID: 627996 View in Reaxys 14/14 Yield
Conditions & References With tetrahydrofuran, lithium aluminium tetrahydride Barlow; Khan; British Journal of Pharmacology and Chemotherapy; vol. 14; (1959); p. 99,101 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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