6. N–G'zvezdochka', 2 keto [Reaxys, Reactions (14); 2016-03-23]

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

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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

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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

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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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