Synthesis of 2-thio-substituted benzothiazoles via a domino condensation/S-arylation/heterocyclization process

J Org Chem. 2011 May 20;76(10):4200-4. doi: 10.1021/jo200535e. Epub 2011 Apr 29.

Abstract

Condensation of carbon disulfide with thiols in the presence of K(2)CO(3) generates carbonotrithioate salts in situ, which undergo coupling with 2-iodoanilines and subsequent intramolecular condensation and elimination under assistance of CuBr to afford 2-thio-substituted benzothiazoles. Both aliphatic and aromatic thiols are compatible with this process, delivering the corresponding heterocycles with good diversity.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzothiazoles / chemical synthesis*
  • Benzothiazoles / chemistry*
  • Cyclization
  • Sulfur / chemistry*

Substances

  • Benzothiazoles
  • Sulfur