Synthesis of tetrasubstituted pyrroles from terminal alkynes and imines

Org Lett. 2013 Jun 21;15(12):3146-9. doi: 10.1021/ol401369d. Epub 2013 Jun 7.

Abstract

Tetrasubstituted pyrroles can be obtained via the reaction of terminal alkynes and imines using (n)BuLi as the base in one step with high chemoselectivity (method 1). Alternatively, the intermediate propargylamines can also react with imines to afford tetrasubstituted pyrroles when using LiHMDS as the base (method 2), which provides a complementary method to construct the pyrroles with different substituents.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alkynes / chemistry*
  • Catalysis
  • Imines / chemistry*
  • Molecular Structure
  • Pargyline / analogs & derivatives
  • Pargyline / chemistry
  • Propylamines / chemistry
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry
  • Stereoisomerism

Substances

  • Alkynes
  • Imines
  • Propylamines
  • Pyrroles
  • propargylamine
  • Pargyline