Brønsted Acid-Catalyzed Synthesis of 1,2,5-Trisubstituted Imidazoles via a Multicomponent Reaction of Vinyl Azides with Aromatic Aldehydes and Aromatic Amines

Jiuling Li*, Xinyu Jia, Ju Qiu, Min Wang, Juan Chen, Minghui Jing, Yifu Xu, Xinhua Zheng* and Hongmei Dai

*School of Medical Sciences, Pingdingshan University, Pingdingshan 467000, People's Republic of China, Email: orgchem90163.com, zhengxinhua70163.com

J. Li, X. Jia, J. Qiu, M. Wang, J. Chen, M. Jing, Y. Xu, X. Zheng, H. Dai, J. Org. Chem., 2022, 87, 13945-13954.

DOI: 10.1021/acs.joc.2c01624

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Abstract

Benzoic acid catalyzes an efficient multicomponent reaction of readily available vinyl azides, aromatic aldehydes, and aromatic amines to provide 1,2,5-trisubstituted imidazoles under metal-free conditions without generating any toxic waste. This convenient approach offers high functional group compatibility.

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proposed mechanism

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Key Words

imidazoles, organocatalysis, multicomponent reactions

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ID: J42-Y2022