Iodine-Mediated Cyclization of Enamines to Imidazole-4-Carboxylic Derivatives with Sequential Removal of Nitrogen Atoms from TMSN₃

Peng Gao*, Huaijuan Chen, Zi-Jing Bai, Sheng Zhang, Mi-Na Zhao, Desuo Yang, Yingchun Li, Jiangwei Zhang and Xiaomei Wang

*Shaanxi Key Laboratory of Phytochemistry, College of Chemistry and Chemical Engineering, Baoji University of Arts and Sciences, Baoji, Shaanxi 721013, P. R. China, Email: gaopeng_hxbjwlxy.edu.cn

P. Gao, H. Chen, Z.-J. Bai, S. Zhang, M.-N. Zhao, D. Yang, Y. Li, J. Zhang, X. Wang, J. Org. Chem., 2021, 86, 10492-10500.

DOI: 10.1021/acs.joc.1c01145

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Abstract

An iodine-mediated oxidative [4+1] cyclization of enamines with TMSN₃ provides 2,5-disubstituted imidazole-4-carboxylic derivatives. Mechanistic studies revealed that the reaction proceeds through a sequential removal of two nitrogen atoms from TMSN₃. The synthetic utility was demonstrated with a gram-scale reaction and various derivatization transformations of the products.

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propose mechanism

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Key Words

imidazoles, iodine

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ID: J42-Y2021