Visible Light-Promoted Three-Component Tandem Annulation for the Synthesis of 2-Iminothiazolidin-4-ones

Wei Guo* , Mingming Zhao, Wen Tan, Lvyin Zheng, Kailiang Tao, Lingxiu Liu, Xinyu Wang, Deliang Chen* and Xiaolin Fan*

*Key Laboratory of Organo-pharmaceutical Chemistry of Jiangxi Province, Gannan Normal University, Ganzhou 341000, China, Email: guoweigw126.com, deliang2211hotmail.com, fanxl2008gnnu.edu.cn

W. Guo, M. Zhao, W. Tan, L. Zheng, K. Tao, L. Liu, X. Wang, D. Chen, X. Fan, J. Org. Chem., 2018, 83, 1402-1413.

DOI: 10.1021/acs.joc.7b02940

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Abstract

A visible light-promoted three-component tandem annulation of α-bromoesters, amines, and aryl/alkyl isothiocyanates provides 2-iminothiazolidin-4-ones at room temperature in the absence of metal and photocatalyst. This [1 + 2 + 2] cyclization strategy offers broad substrate scope, excellent functional group tolerance, mild reaction conditions, step-economy, and simple operation.

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proposed mechanism

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Key Words

N-heterocycles, S-heterocycles, multicomponent reactions, photochemistry

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ID: J42-Y2018