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Published on: June 21, 2017
Metal-free oxidative cyclization of acetophenones with diamines: a facile access to phenylpyridines
Rohit Sharma1, Neha Patel2, Ram A Vishwakarma1
1Medicinal Chemistry Division, CSIR - Indian Institute of Integrative Medicine, Canal Road, Jammu-180001, India. sbharate@iiim.ac.in and Academy of Scientific & Innovative Research (AcSIR), CSIR - Indian Institute of Integrative Medicine, Canal Road, Jammu-180001, India.
Abstract:
An efficient metal-free access to 2- and 3-phenylpyridines via oxidative coupling of acetophenones or phenylacetones with 1,3-diaminopropane has been described. The reaction involves shorter reaction time, excellent yields and a broad substrate scope. The reaction proceeds via the formation of imine, which further undergoes oxidative C-N bond cleavage, C-C bond formation and oxidation to give a pyridine skeleton. The quantum chemical calculations identified the transition state for the reaction and helped in tracing the reaction mechanism.
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