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

Described is a visible light-promoted three-component tandem annulation of amines, aryl/alkyl isothiocyanates, and α-bromoesters to form 2-iminothiazolidin-4-ones in the absence of metal and photocatalyst at room temperature. This [1 + 2 + 2] cyclization strategy involves visible light-promoted C–S/...

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Bibliographic Details
Published in:Journal of organic chemistry 2018-02, Vol.83 (3), p.1402-1413
Main Authors: Guo, Wei, Zhao, Mingming, Tan, Wen, Zheng, Lvyin, Tao, Kailiang, Liu, Lingxiu, Wang, Xinyu, Chen, Deliang, Fan, Xiaolin
Format: Article
Language:English
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Summary:Described is a visible light-promoted three-component tandem annulation of amines, aryl/alkyl isothiocyanates, and α-bromoesters to form 2-iminothiazolidin-4-ones in the absence of metal and photocatalyst at room temperature. This [1 + 2 + 2] cyclization strategy involves visible light-promoted C–S/C–N bond formation and features a powerful approach to the synthesis of 2-iminothiazolidin-4-ones with broad substrate scope, excellent functional group tolerance, mild reaction conditions, step-economy, and simple operation, which also has potential applications in the pharmaceutical industry. UV–vis spectroscopy indicates that an in situ-generated H-bonding electron donor–acceptor (EDA) complex probably acts as the photocatalyst, facilitating the reaction process.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.7b02940