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A rapid and efficient method for the reduction of quinoxalines

✍ Scribed by Andrew M. McKinney; Kevin R. Jackson; Ralph Nicholas Salvatore; Elena-Maria Savrides; Mary Jane Edattel; Terrence Gavin

Publisher
Journal of Heterocyclic Chemistry
Year
2005
Tongue
English
Weight
42 KB
Volume
42
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Mono and di‐substituted alkyl and aryl quinoxalines are rapidly reduced in high yield to their respective 1,2,3,4‐tetrahydro‐derivatives by borane in THF solution. In the case of the 2,3‐di‐substituted compounds, reduction is stereoselective yielding exclusively the cis‐isomers. Sodium borohydride in acetic acid also reduces alkyl and aryl quinoxalines, but proceeds with lower yields and often produces side products. Sodium borohydride in ethanol reduces quinoxaline and 2‐methylquinoxaline in high yield; however, the reaction is very slow, whereas 2,3‐dialkyl and 2‐aryl quinoxalines are not efficiently reduced by sodium borohydride in ethanol.

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