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I2-Mediated Intramolecular C-H Amidation for the Synthesis of N-Substituted Benzimidazoles

Zhiyuan Hu, Ting Zhao, Manman Wang, Jie Wu, Wenquan Yu* and Junbiao Chang*

*College of Chemistry and Molecular Engineering, Zhengzhou University, Zhengzhou, Henan Province 450001, People’s Republic of China, Email: wenquan_yuzzu.edu.cn, changjunbiaozzu.edu.cn

Z. Hu, T. Zhao, M. Wang, J. Wu, W. Yu, J. Chang, J. Org. Chem., 2017, 82, 3152-3158.

DOI: 10.1021/acs.joc.7b00142 (free Supporting Information)


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Abstract

A practical intramolecular C-H amidation methodology using molecular iodine under basic conditions enables a transition-metal-free cyclization of crude imines for the sequential synthesis of N-protected benzimidazoles without purification of less stable condensation intermediates. The required imine substrates were readily obtained by condensation of simple o-phenylenediamine derivatives and a broad range of aldehydes.

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Key Words

Benzimidazoles, Iodine


ID: J42-Y2017