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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Veröffentlicht in: | Journal of organic chemistry 2018-02, Vol.83 (3), p.1402-1413 |
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Hauptverfasser: | , , , , , , , , |
Format: | Artikel |
Sprache: | eng |
Online-Zugang: | Volltext |
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Zusammenfassung: | 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. |
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ISSN: | 0022-3263 1520-6904 |
DOI: | 10.1021/acs.joc.7b02940 |