Copper(II)-Mediated Aerobic Synthesis of Imidazo[1,2-a]pyridines via Cascade Aminomethylation/Cycloisomerization of Alkynes

Irina V. Rassokhina, Valerii Z. Shirinian, Igor V. Zavarzin, Vladimir Gevorgyan, Yulia A. Volkova

Research output: Contribution to journalArticle

39 Scopus citations

Abstract

A single copper(II)-catalyzed three-component cascade aminomethylation/cycloisomerization of propiolates to form imidazo[1,2-a]pyridines was explored. A straightforward method was developed for the practical synthesis of functionalized imidazo[1,2-a]pyridines from benzaldehydes, 2-aminopyridines, and propiolate derivatives catalyzed by Cu(OAc)2 hydrate in the presence of air. The protocol is marked by excellent yields, functional group tolerance, and, above all, adaptability to synthesize imidazo[1,2-a]pyridine-based drug molecules such as Alpidem.

Original languageEnglish (US)
Pages (from-to)11212-11218
Number of pages7
JournalJournal of Organic Chemistry
Volume80
Issue number21
DOIs
StatePublished - Nov 6 2015
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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