A convenient preparation of xanthene dyes

J Org Chem. 2005 Aug 19;70(17):6907-12. doi: 10.1021/jo051002a.

Abstract

A facile synthetic route utilizing readily available reagents affords a series of regioisomerically pure xanthene dye derivatives. Advantages include relatively mild conditions and good to excellent yields. Nonpolar, highly crystalline intermediates are isolable by standard chromatographic techniques. The intermediates are in the requisite xanthene oxidation state, thus avoiding the need for relatively inefficient oxidation chemistry and/or harsh conditions. During the course of this work, a new boron-mediated 1,2-aryl migration reaction was discovered.

Publication types

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

MeSH terms

  • Coloring Agents / chemical synthesis*
  • Coloring Agents / chemistry
  • Magnetic Resonance Spectroscopy
  • Models, Molecular
  • Spectrometry, Mass, Matrix-Assisted Laser Desorption-Ionization
  • Xanthenes / chemical synthesis*
  • Xanthenes / chemistry

Substances

  • Coloring Agents
  • Xanthenes