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Molecules 2016, 21(10), 1304; doi:10.3390/molecules21101304

Nucleophilic Substitution on 2-Monosubstituted Quinoxalines Giving 2,3-Disubstituted Quinoxalines: Investigating the Effect of the 2-Substituent

Department of Chemistry, Faculty of Science and Agriculture, University of Limpopo, Private Bag X 1106, Sovenga 0727, South Africa
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Author to whom correspondence should be addressed.
Academic Editor: Philippe Belmont
Received: 30 August 2016 / Revised: 15 September 2016 / Accepted: 23 September 2016 / Published: 30 September 2016
(This article belongs to the Collection Heterocyclic Compounds)
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Abstract

An investigation on the effect of substituent at the 2-position of mono-substituted quinoxalines in the synthesis of di-substituted quinoxaline derivatives via nucleophilic substitution reactions, is reported. Di-substituted quinoxalines bearing aryl-alky, aryl-aryl, aryl-heteroaryl, aryl-alkynyl, and amino-alkyl substituents were prepared in moderate to good yields. 2-Monosubstituted quinoxalines bearing a phenyl and butyl substituent reacted readily with alkyl-, aryl-, heteroaryl- and alkynyl- nucluephiles, giving di-substituted quinoxalines. 2-Monosubstituted quinoxalines bearing an amine and alkynyl substituent only reacted with alkyl nucleophiles. Oxidative rearomatization to give 2,3-disubstituted quinoxaline products occurred in atmospheric O2. View Full-Text
Keywords: 2,3-disubsituted quinoxaline; nucleophilic substitution; oxidative rearomatization 2,3-disubsituted quinoxaline; nucleophilic substitution; oxidative rearomatization
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Ndlovu, N.T.; Nxumalo, W. Nucleophilic Substitution on 2-Monosubstituted Quinoxalines Giving 2,3-Disubstituted Quinoxalines: Investigating the Effect of the 2-Substituent. Molecules 2016, 21, 1304.

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