Cu-Catalyzed and iodine mediated synthesis of thioaurones via in situ C-S bond generation using xanthate as a sulfur surrogate

Org Biomol Chem. 2022 Sep 28;20(37):7405-7409. doi: 10.1039/d2ob01211a.

Abstract

An efficient method for synthesizing thioaurones has been developed using xanthate as an odorless sulfur surrogate. This reaction's key success lies in the use of iodine as a reagent, which promotes the α-iodination followed by cyclization of saturated ketones. This methodology has also been demonstrated with less reactive 2'-bromochalcones in good yield. Synthesis of the red isomer of indigo, i.e. a thia-analog of indirubin, was also achieved.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Catalysis
  • Indigo Carmine
  • Iodides
  • Iodine* / chemistry
  • Ketones / chemistry
  • Molecular Structure
  • Sulfur / chemistry

Substances

  • Iodides
  • Ketones
  • Sulfur
  • Iodine
  • Indigo Carmine