Efficient one-pot synthesis of polyfunctionalized thiophenes via an amine-mediated ring opening of EWG-activated 2-methylene-1,3-dithioles

Org Lett. 2007 Nov 8;9(23):4845-8. doi: 10.1021/ol7021752. Epub 2007 Oct 11.

Abstract

An amine-mediated ring-opening reaction of EWG-activated 2-methylene-1,3-dithioles (EWG = electron-withdrawing group) was disclosed, and a new route to highly substituted thiophenes was developed via the ring opening of 1,3-dithioles and subsequent intramolecular annulation and amine substitution. This one-pot reaction could proceed efficiently under mild conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Amines / chemistry*
  • Crystallography, X-Ray
  • Ethylamines / chemistry
  • Methylation
  • Models, Molecular
  • Molecular Structure
  • Thiophenes / chemical synthesis*
  • Thiophenes / chemistry
  • Toluene / analogs & derivatives*
  • Toluene / chemistry

Substances

  • Amines
  • Ethylamines
  • Thiophenes
  • Toluene
  • dithiol