Convenient synthesis of benzothiazoles and benzimidazoles through Brønsted acid catalyzed cyclization of 2-amino thiophenols/anilines with β-diketones

Org Lett. 2014 Feb 7;16(3):764-7. doi: 10.1021/ol403475v. Epub 2014 Jan 10.

Abstract

Brønsted acid catalyzed cyclization reactions of 2-amino thiophenols/anilines with β-diketones under oxidant-, metal-, and radiation-free conditions are described. Various 2-substituted benzothiazoles/benzimidazoles are obtained in satisfactory to excellent yields. Different groups such as methyl, chloro, nitro, and methoxy linked on benzene rings were tolerated under the optimized reaction conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds / chemistry*
  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / chemistry
  • Benzothiazoles / chemical synthesis*
  • Benzothiazoles / chemistry
  • Catalysis
  • Cyclization
  • Ketones / chemistry*
  • Molecular Structure
  • Phenols / chemistry*
  • Stereoisomerism
  • Sulfhydryl Compounds / chemistry*

Substances

  • Aniline Compounds
  • Benzimidazoles
  • Benzothiazoles
  • Ketones
  • Phenols
  • Sulfhydryl Compounds
  • thiophenol