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

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

Journal

Journal of Organic Chemistry
ISSN: 1520-6904 , E-ISSN: 0022-3263

Output data

Year: 2015, Volume: 80, Number: 21, Pages: 11212-11218 Pages count : 7 DOI: 10.1021/acs.joc.5b02102

Authors

Rassokhina Irina V. ¹ , Shirinian Valerii Z. ¹ , Zavarzin Igor V. ¹ , Gevorgyan Vladimir ² , Volkova Yulia A. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991 Moscow, Russia
2	Department of Chemistry, University of Illinois at Chicago, 845 West Taylor Street, Room 4500, Chicago, Illinois 60607, United States

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.

Rassokhina I.V. , Shirinian V.Z. , Zavarzin I.V. , Gevorgyan V. , Volkova Y.A.
Copper(II)-Mediated Aerobic Synthesis of Imidazo[1,2-a]pyridines via Cascade Aminomethylation/Cycloisomerization of Alkynes
Journal of Organic Chemistry. 2015. V.80. N21. P.11212-11218. DOI: 10.1021/acs.joc.5b02102 WOS Scopus OpenAlex

Web of science:	WOS:000364435000085
Scopus:	2-s2.0-84946763271
OpenAlex:	W2266536744

DB	Citing
OpenAlex	50
Scopus	49
Web of science	50