Synthesis of benzo[c]xanthones from 2-benzylidene-1-tetralones by the ultraviolet radiation-mediated tandem reaction

J Org Chem. 2008 Jul 18;73(14):5606-8. doi: 10.1021/jo8008929. Epub 2008 Jun 14.

Abstract

A facile one-pot method to prepare benzo[c]xanthones from readily accessible benzylidene-1-tetralones by the ultraviolet radiation-mediated tandem reaction is reported. The overall transformation presumably involves cis-trans isomerization, oxa-6pi electrocyclization, singlet oxygen ene reaction, dehydration, and aromatization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzene / chemistry*
  • Crystallography, X-Ray
  • Cyclization
  • Models, Molecular
  • Molecular Structure
  • Oxidation-Reduction
  • Photochemistry
  • Tetralones / chemistry*
  • Ultraviolet Rays*
  • Xanthones / chemical synthesis*
  • Xanthones / chemistry

Substances

  • Tetralones
  • Xanthones
  • 2-benzylidenetetralone
  • Benzene