Synthesis of 1,3-Disubstituted Imidazo[1,5-a]pyridines from Amino Acids via Catalytic Decarboxylative Intramolecular Cyclization

Huiqiao Wang, Wentao Xu, Lilan Xin, Wenmin Liu, Zhiqiang Wang* and Kun Xu*

*College of Chemistry and Pharmaceutical Engineering, Nanyang Normal University, Nanyang, Henan 473061, P. R. China, Email: smile_126qq.com, xukunnynu.edu.cn

H. Wang, W. Xu, L. Xin, W. Liu, Z. Wang, K. Xu, J. Org. Chem., 2016, 81, 3681-3687.

DOI: 10.1021/acs.joc.6b00343

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Abstract

A copper/iodine cocatalyzed decarboxylative cyclization of α-amino acids with either 2-benzoylpyridines or 2-benzoylquinolines provides 1,3-disubstituted imidazo[1,5-a]pyridines and 1,3-disubstituted imidazo[1,5-a]quinolines in excellent yields.

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plausible mechanism

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Copper-Catalyzed Oxidative Amination of sp³ C-H Bonds under Air: Synthesis of 1,3-Diarylated Imidazo[1,5-a]pyridines

H. Wang, W. Xu, Z. Wang, L. Yu, K. Xu, J. Org. Chem., 2015, 80, 1856-1865.

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Key Words

imidazo[1,5-a]pyridines, iodine, di-tert-butyl peroxide

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ID: J42-Y2016