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Metal-Free Synthesis of Benzimidazoles via Oxidative Cyclization of D-Glucose with o-Phenylenediamines in Water

Dineshkumar Raja, Abigail Philips, Pushbaraj Palani, Wei-Yu Lin, Sundaramurthy Devikala* and Gopal Chandru Senadi*

*Department of Chemistry, SRM Institute of Science and Technology, SRM Nagar, Chengalpattu District, Kattankulathur, Tamil Nadu 603203, India, Email: devikalssrmist.edu.in, chandrugsrmist.edu.in

D. Raja, A. Philips, P. Palani, W.-Y. Lin, S. Devikala, G. C. Senadi, J. Org. Chem., 2020, 85, 11531-11540.

DOI: 10.1021/acs.joc.0c01053 (free Supporting Information)


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Abstract

D-Glucose can be used as an efficient C1 synthon in the synthesis of benzimidazoles from o-phenylenediamines via an oxidative cyclization strategy. This method offers broad functional group tolerance, a biorenewable methine source, excellent reaction yields, a short reaction time, and water as an environmentally benign solvent.

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proposed mechanism



Key Words

benzimidazoles, green chemistry, TBHP


ID: J42-Y2020