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Accessing Benzimidazoles via a Ring Distortion Strategy: An Oxone Mediated Tandem Reaction of 2-Aminobenzylamines

Santanu Hati, Pratip Kumar Dutta, Sanjay Dutta, Parthapratim Munshi and Subhabrata Sen*

*Department of Chemistry, School of Natural Sciences, Shiv Nadar University, Chithera, Dadri, Gautam Buddha Nagar, UP 201314, India, Email: subhabrata.sensnu.edu.in

S. Hati, P. K. Dutta, S. Dutta, P. Munshi, S. Sen, Org. Lett., 2016, 18, 3090-3093.

DOI: 10.1021/acs.orglett.6b01217 (free Supporting Information)


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Abstract

An oxone mediated tandem transformation of 2-aminobenzylamines to 2-substituted benzimidazoles occurs at room temperature with aromatic, heteroaromatic, and aliphatic aldehydes. Initial condensation of 2-aminobenzylamine with appropriate aldehydes afforded a tetrahydroquinazoline intermediate which underwent oxone-mediated ring distortion to afford the desired compounds in good yields.

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Key Words

benzimidazoles, oxone


ID: J54-Y2016