Regioselective synthesis of tetrasubstituted pyrroles by 1,3-dipolar cycloaddition and spontaneous decarboxylation

Org Lett. 2009 Jan 1;11(1):17-20. doi: 10.1021/ol8022193.

Abstract

We developed a novel regioselective synthesis of tetrasubstituted pyrroles via the classic 1,3-dipolar cycloaddition of alpha,beta-unsaturated benzofuran-3(2H)-one and azlactones (1) followed by spontaneous decarboxylation. The complete regiochemical control of tetrasubstituted pyrroles was confirmed by the orthogonal synthesis of complementary regioisomers (7a and 7b) simply by using different azlactones (1a and 1b, respectively).

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzofurans / chemistry
  • Crystallography, X-Ray
  • Cyclization
  • Decarboxylation
  • Lactones / chemistry
  • Models, Molecular
  • Molecular Structure
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry*
  • Stereoisomerism

Substances

  • Benzofurans
  • Lactones
  • Pyrroles