Photoredox-Promoted Selective Synthesis of C‑5 Thiolated 2‑Aminothiazoles from Terminal Alkynes

A mild photoredox approach enabling the first one-step synthesis of thiolated 2-aminothiazoles has been reported. Notably, the incorporation of thio group on electron-rich heteroarenes such as aminothiazoles via conventional nucleophilic aromatic substitution (SNAr) presents a significant challenge...

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Bibliographic Details
Published in:Organic letters 2022-10, Vol.24 (42), p.7757-7762
Main Authors: Ganie, Majid Ahmad, Bhat, Muneer-ul-Shafi, Rizvi, Masood Ahmad, Raheem, Shabnam, Shah, Bhahwal Ali
Format: Article
Language:English
Subjects:
Alkynes
Electrons
Thiazoles
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Summary:A mild photoredox approach enabling the first one-step synthesis of thiolated 2-aminothiazoles has been reported. Notably, the incorporation of thio group on electron-rich heteroarenes such as aminothiazoles via conventional nucleophilic aromatic substitution (SNAr) presents a significant challenge owing to polarity mismatch. Herein, we present a remarkable site-selective installation of thio group at the C-5 position of the electron-rich aminothiazole skeleton and successfully used them for the postfunctionalization of drugs and natural products.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c03064