Bharate Jaideep B, Abbat Sheenu, Bharatam Prasad V, Vishwakarma Ram A, Bharate Sandip B
Medicinal Chemistry Division, CSIR - Indian Institute of Integrative Medicine, Canal Road, Jammu 180001, India.
Org Biomol Chem. 2015 Jul 28;13(28):7790-4. doi: 10.1039/c5ob00776c. Epub 2015 Jun 23.
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.
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。