Efficient two-step synthesis of 9-aryl-6-hydroxy-3H-xanthen-3-one fluorophores

J Org Chem. 2005 Oct 28;70(22):9051-3. doi: 10.1021/jo051243i.

Abstract

[reaction: see text] A two-step method for the synthesis of 9-aryl-6-hydroxy-3H-xanthen-3-one fluorophores involving condensation of aryl aldehydes and fluororesorcinol is shown to proceed through a triarylmethane intermediate. The condensation is complicated by retro-Friedel-Crafts reactions which can be minimized by controlling the amount of acid. The xanthenone ring system is prepared by a final oxidative cyclization with DDQ.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Benzaldehydes / chemistry
  • Cyclization
  • Fluorine / chemistry*
  • Hydroxylation
  • Molecular Structure
  • Oxidation-Reduction
  • Xanthenes / chemical synthesis
  • Xanthenes / chemistry*

Substances

  • Benzaldehydes
  • Xanthenes
  • Fluorine