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溴化亚铜催化2-氨基吡啶与肉桂醛的需氧氧化偶联反应:直接合成3-甲酰基-2-苯基-咪唑并[1,2-a]吡啶

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

作者信息

Bharate Jaideep B, Abbat Sheenu, Bharatam Prasad V, Vishwakarma Ram A, Bharate Sandip B

机构信息

Medicinal Chemistry Division, CSIR - Indian Institute of Integrative Medicine, Canal Road, Jammu 180001, India.

出版信息

Org Biomol Chem. 2015 Jul 28;13(28):7790-4. doi: 10.1039/c5ob00776c. Epub 2015 Jun 23.

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.

摘要

溴化铜催化的2-氨基吡啶与肉桂醛的有氧氧化偶联直接导致3-甲酰基-2-苯基-咪唑并[1,2-a]吡啶的形成。进行量子化学计算以追踪反应机理并深入了解可能的反应途径。2-氨基吡啶与肉桂醛偶联生成(E)-3-苯基-3-(吡啶-2-基氨基)丙烯醛IV作为关键中间体,该中间体发生C-N键形成反应生成3-甲酰基-2-苯基-咪唑并[1,2-a]吡啶。

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引用本文的文献

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Recent advances on the transition-metal-catalyzed synthesis of imidazopyridines: an updated coverage.
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