M. M. El’chaninov, A. A. Achkasova, I. M. El’chaninov
Dec 17, 2014
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Journal
Russian Journal of Organic Chemistry
Abstract
Abstract2,3-Diaminopyridine and furfural in the conditions of Weidenhagen reaction give rise to 2-(furan-2-yl)-1(3)H-imidazo[4,5-b]pyridine, whose methylation in KOH-acetonee system affords isomeric 1-methyl-2-(furan-2-yl)-1H- and 3-methyl-2-(furan-2-yl)-3H-imidazo[4,5-b]pyridines. At the electrophilic substitution of the 1-methyl isomer (nitration, bromination, sulfation, formylation, acylation) depending on the conditions either furan ring, or pyridine fragment suffer the electrophilic attack. At its quaternization with methyl iodide in benzene N-methylpyridinium salt is obtained.