Gold(III) chloride catalysed synthesis of 5-alkylidene-dihydrothiazoles

Org Biomol Chem. 2011 Jul 7;9(13):4791-4. doi: 10.1039/c1ob05509g. Epub 2011 May 13.

Abstract

A two step synthesis of dihydrothiazoles is presented. First, the previously unknown N-propargylic dithiocarboimidates are produced in good yields from easily available, cheap starting materials. The subsequent gold catalysed ring closure is fast and efficient, leading to dihydrothiazoles through a cascade of 5-exo-dig cyclisation and 1,3-alkyl migration. The yields range from 74% to 95%.

MeSH terms

  • Alkylation
  • Catalysis
  • Gold Compounds / chemistry*
  • Hydrogenation
  • Molecular Structure
  • Thiazoles / chemical synthesis*

Substances

  • Gold Compounds
  • Thiazoles
  • gold chloride