Copper-catalyzed three-component synthesis of benzothiazolethiones from o-iodoanilines, isocyanide, and potassium sulfide

Org Lett. 2015 Jan 2;17(1):34-7. doi: 10.1021/ol503186w. Epub 2014 Dec 12.

Abstract

An efficient copper catalyzed strategy for the synthesis of a variety of benzothiazolethione derivatives has been developed. In the presence of CuCl, the three-component reaction of o-iodoanilines and K2S with p-toluenesulfonylmethyl isocyanide proceeded smoothly to obtain the corresponding benzothiazolethiones in good to excellent isolated yields. Notably, isocyanide functioned as a carbon source and K2S functioned as a sulfur source in this reaction.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry*
  • Benzothiazoles / chemical synthesis*
  • Benzothiazoles / chemistry
  • Catalysis
  • Combinatorial Chemistry Techniques
  • Copper / chemistry*
  • Cyanides / chemistry*
  • Molecular Structure
  • Potassium / chemistry*
  • Sulfides / chemistry*
  • Thiazolidines / chemical synthesis*
  • Thiazolidines / chemistry

Substances

  • Aniline Compounds
  • Benzothiazoles
  • Cyanides
  • Sulfides
  • Thiazolidines
  • thiazoline-2-thione
  • 3-iodoaniline
  • Copper
  • cuprous chloride
  • Potassium