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

Bharate, Jaideep B. ; Abbat, Sheenu ; Bharatam, Prasad V. ; Vishwakarma, Ram A. ; Bharate, Sandip B. (2015) CuBr catalyzed aerobic oxidative coupling of 2-aminopyridines with cinnamaldehydes: direct access to 3-formyl-2-phenyl-imidazo[1,2-a]pyridines Organic & Biomolecular Chemistry, 13 (28). pp. 7790-7794. ISSN 1477-0520

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Official URL: http://doi.org/10.1039/C5OB00776C

Related URL: http://dx.doi.org/10.1039/C5OB00776C

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.

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ID Code:116409
Deposited On:12 Apr 2021 09:33
Last Modified:12 Apr 2021 09:33

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