Synthesis and reactivity of 2-(furan-2-yl)-1(3)H-imidazo[4,5-b]pyridine

Synthesis and reactivity of 2-(furan-2-yl)-1(3)H-imidazo[4,5-b]pyridine

2,3-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)-1 H - and 3-methyl-2-(furan-2-yl)-3 H -imidazo[4,5- b ]pyridines. At the electrop...

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Veröffentlicht in:Russian journal of organic chemistry 2014-11, Vol.50 (11), p.1663-1666
Hauptverfasser: Elchaninov, M. M., Achkasova, A. A., Elchaninov, I. M.
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container_issue 11
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container_title Russian journal of organic chemistry
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creator Elchaninov, M. M.
Achkasova, A. A.
Elchaninov, I. M.
description 2,3-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)-1 H - and 3-methyl-2-(furan-2-yl)-3 H -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.
doi_str_mv 10.1134/S1070428014110207
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Organic Chemistry
title Synthesis and reactivity of 2-(furan-2-yl)-1(3)H-imidazo[4,5-b]pyridine
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