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A rapid and efficient method for the reduction of quinoxalines
Author(s) -
McKinney Andrew M.,
Jackson Kevin R.,
Salvatore Ralph Nicholas,
Savrides ElenaMaria,
Edattel Mary Jane,
Gavin Terrence
Publication year - 2005
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570420546
Subject(s) - chemistry , sodium borohydride , quinoxaline , yield (engineering) , aryl , alkyl , ethanol , acetic acid , borane , medicinal chemistry , stereoselectivity , organic chemistry , borohydride , catalysis , materials science , metallurgy
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.