Access to N-thioalkenyl and N-(o-thio)aryl-benzimidazol-2-ones by ring opening of thiazolobenzimidazolium and benzimidazobenzothiazolium salts and C-O bond cleavage of an alkoxide

J Org Chem. 2015 Mar 20;80(6):3233-41. doi: 10.1021/acs.joc.5b00221. Epub 2015 Mar 11.

Abstract

We report herein the synthesis of highly functionalized 1,3-dihydro-2H-benzimidazol-2-ones via a ring opening of thiazolo[3,2-a]benzimidazolium or benzimidazo[2,1-b][1,3]benzothiazol-6-ium salts and an unusual C-O bond cleavage of an alkoxide. A large variety of benzimidazolones bearing an original N-thioalkenyl or N-(o-thio)aryl group was obtained in high yields. The developed chemistry provides efficient and rapid access to the privileged benzimidazol-2-one scaffold.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzimidazoles / chemical synthesis*
  • Benzimidazoles / chemistry*
  • Molecular Structure
  • Oxides / chemistry*
  • Salts / chemistry
  • Thiazoles / chemistry*

Substances

  • Benzimidazoles
  • Oxides
  • Salts
  • Thiazoles
  • 1-(2',6'-difluorophenyl)-1H,3H-thiazolo(3,4-a)benzimidazole
  • benzimidazol-2-one