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

Org Lett. 2022 Oct 28;24(42):7757-7762. doi: 10.1021/acs.orglett.2c03064. Epub 2022 Oct 14.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes*
  • Electrons
  • Thiazoles*

Substances

  • Alkynes
  • 2-aminothiazole
  • Thiazoles