Construction of Imidazole-Fused-Ring Systems by Iron-Catalyzed C(sp³)-H Amination-Cyclization under Aerobic Conditions

Jiangling Peng, Shijia Li, Junwei Huang, Qianli Meng, Lixin Wang, Wenlong Xin, Weini Li, Wei Zhou*, Lanyue Zhang*

*School of Biomedical and Pharmaceutical Sciences, Guangdong University of Technology, Guangzhou, Guangdong 510006, China, Email: zhou_weigdut.edu.cn, zhanglanyuegdut.edu.cn

J. Peng, S. Li, J. Huang, Q. Meng, L. Wang, W. Xin, W. Li, W. Zhou, L. Zhang, J. Org. Chem., 2023, 88, 16581-16588.

DOI: 10.1021/acs.joc.3c02078

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Abstract

An iron-catalyzed efficient C-H amination for the construction of imidazole-fused-ring systems can be conducted in anisole as green solvent with water as the only byproduct. The reaction provides Imidazo[1,5-a]pyridines, imidazo[5,1-b]oxazoles, imidazo[5,1-b]thiazoles, imidazo[1,5-a]pyrazines, and imidazo[1,5-a]imidazoles.

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proposed mechanism

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Key Words

imidazo[1,5-a]pyridines, oxygen

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ID: J42-Y2023