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Issue 28, 2015
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CuBr catalyzed aerobic oxidative coupling of 2-aminopyridines with cinnamaldehydes: direct access to 3-formyl-2-phenyl-imidazo[1,2-a]pyridines

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Abstract

Copper bromide catalyzed aerobic oxidative coupling of 2-aminopyridines with cinnamaldehydes directly led to the formation of 3-formyl-2-phenyl-imidazo[1,2-a]pyridines. The quantum chemical calculations were performed to trace the reaction mechanism and get insights into the possible reaction pathway. 2-Aminopyridines on coupling with cinnamaldehyde generate (E)-3-phenyl-3-(pyridin-2-ylamino)acrylaldehyde IV as a key intermediate, which undergoes C–N bond formation reaction to produce 3-formyl-2-phenyl-imidazo[1,2-a]pyridines.

Graphical abstract: CuBr catalyzed aerobic oxidative coupling of 2-aminopyridines with cinnamaldehydes: direct access to 3-formyl-2-phenyl-imidazo[1,2-a]pyridines

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Article information


Submitted
17 Apr 2015
Accepted
09 Jun 2015
First published
09 Jun 2015

Org. Biomol. Chem., 2015,13, 7790-7794
Article type
Paper
Author version available

CuBr catalyzed aerobic oxidative coupling of 2-aminopyridines with cinnamaldehydes: direct access to 3-formyl-2-phenyl-imidazo[1,2-a]pyridines

J. B. Bharate, S. Abbat, P. V. Bharatam, R. A. Vishwakarma and S. B. Bharate, Org. Biomol. Chem., 2015, 13, 7790
DOI: 10.1039/C5OB00776C

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