TY - JOUR
T1 - Copper(II)-Mediated Aerobic Synthesis of Imidazo[1,2-a]pyridines via Cascade Aminomethylation/Cycloisomerization of Alkynes
AU - Rassokhina, Irina V.
AU - Shirinian, Valerii Z.
AU - Zavarzin, Igor V.
AU - Gevorgyan, Vladimir
AU - Volkova, Yulia A.
N1 - Publisher Copyright:
© 2015 American Chemical Society.
PY - 2015/11/6
Y1 - 2015/11/6
N2 - 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.
AB - 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.
UR - http://www.scopus.com/inward/record.url?scp=84946763271&partnerID=8YFLogxK
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U2 - 10.1021/acs.joc.5b02102
DO - 10.1021/acs.joc.5b02102
M3 - Article
C2 - 26457968
AN - SCOPUS:84946763271
SN - 0022-3263
VL - 80
SP - 11212
EP - 11218
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 21
ER -