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Metal-Free Oxidative Amidation of 2-Oxoaldehydes: A Facile Access to α-Ketoamides

Nagaraju Mupparapu, Shahnawaz Khan, Satyanarayana Battula, Manoj Kushwaha, Ajai Prakash Gupta, Qazi Naveed Ahmed* and Ram A. Vishwakarma*

*Medicinal Chemistry Division, Academy of Scientific and Innovative Research (AcSIR), Indian Institute of Integrative Medicine (IIIM), Jammu, Jammu and Kashmir 180016, India, Email: naqaziiiim.ac.in, ramiiim.ac.in

N. Mupparapu, S. Khan, S. Battula, M. Kushwaha, A. P. Gupta, Q. N. Ahmed, R. A. Vishwakarma, Org. Lett., 2014, 16, 1152-1155.

DOI: 10.1021/ol5000204 (free Supporting Information)


Abstract

A dimethyl sulfoxide (DMSO)-promoted oxidative amidation reaction between 2-oxoaldehydes and amines under metal-free conditions enables an efficient synthesis of α-ketoamides. Mechanistic studies supported an iminium ion intermediate that reacts with DMSO to provide the C1-oxygen atom of the product.

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Key Words

Oxidative Amidation, DMSO


ID: J54-Y2014