Brønsted acid catalyzed and NIS-promoted cyclization of diynones: selective synthesis of 4-pyrone, 4-pyridone, and 3-pyrrolone derivatives

J Org Chem. 2013 Dec 6;78(23):12018-28. doi: 10.1021/jo402055a. Epub 2013 Nov 20.

Abstract

Brønsted acid catalyzed tandem cyclization was found to be highly effective for the preparation of a series of polysubstituted 4-pyrones from diynones (yield up to 99%). 4-Pyridone and 3-pyrrolone derivatives were also selectively synthesized by employing NIS and/or Brønsted acid. NIS as an electrophilic reagent could promote these reactions efficiently and rapidly under very mild reaction conditions.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Acids / chemistry*
  • Catalysis
  • Cyclization
  • Ketones / chemistry*
  • Molecular Structure
  • Pyridones / chemical synthesis*
  • Pyridones / chemistry
  • Pyrones / chemical synthesis*
  • Pyrones / chemistry
  • Pyrroles / chemical synthesis*
  • Pyrroles / chemistry

Substances

  • Acids
  • Ketones
  • Pyridones
  • Pyrones
  • Pyrroles
  • 4-pyridone