2-单取代喹喔啉发生亲核取代反应生成2,3-二取代喹喔啉：研究2-取代基的影响。

Ndlovu Ndumiso Thamsanqa, Nxumalo Winston

Department of Chemistry, Faculty of Science and Agriculture, University of Limpopo, Private Bag X 1106, Sovenga 0727, South Africa.

Molecules. 2016 Sep 30;21(10):1304. doi: 10.3390/molecules21101304.

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.

报道了一项关于单取代喹喔啉2位取代基在通过亲核取代反应合成二取代喹喔啉衍生物中的作用的研究。制备了带有芳基-烷基、芳基-芳基、芳基-杂芳基、芳基-炔基和氨基-烷基取代基的二取代喹喔啉，产率适中至良好。带有苯基和丁基取代基的2-单取代喹喔啉很容易与烷基、芳基、杂芳基和炔基亲核试剂反应，生成二取代喹喔啉。带有胺和炔基取代基的2-单取代喹喔啉仅与烷基亲核试剂反应。在大气中的氧气中发生氧化重排生成2,3-二取代喹喔啉产物。