Synthesis of γ-benzopyranone by TfOH-promoted regioselective cyclization of o-alkynoylphenols

Org Lett. 2011 Sep 2;13(17):4526-9. doi: 10.1021/ol2016934. Epub 2011 Aug 3.

Abstract

Regioselective cyclization of o-alkynoylphenols forming γ-benzopyranones has been demonstrated. Trifluoromethanesulfonic acid (TfOH) induced 6-endo cyclization of o-alkynoylphenols without forming 5-exo cyclized benzofuranone derivatives to provide the corresponding γ-benzopyranones in high yields.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzopyrans / chemical synthesis*
  • Benzopyrans / chemistry
  • Cyclization
  • Mesylates / chemistry*
  • Molecular Structure
  • Phenols / chemistry*
  • Stereoisomerism

Substances

  • Benzopyrans
  • Mesylates
  • Phenols
  • trifluoromethanesulfonic acid