Improved Xanthone Synthesis, Stepwise Chemical Redox Cycling

Org Lett. 2019 Jan 4;21(1):206-209. doi: 10.1021/acs.orglett.8b03661. Epub 2018 Dec 24.

Abstract

A base-catalyzed direct oxidation of rhodamine, carborhodamine, and siliconrhodamine pyronines to the corresponding xanthones is studied. This methodology utilizes addition of water to split pyronines into xanthone and reduced xanthene, the latter of which is returned to pyronine by oxidation with iodine. The transformation is general, working on the three most recalcitrant versions of N, N, N', N'-tetramethylpyronines in good to excellent yields.

Publication types

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

MeSH terms

  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Molecular Structure
  • Oxidation-Reduction
  • Xanthones / chemical synthesis*
  • Xanthones / chemistry

Substances

  • Fluorescent Dyes
  • Xanthones
  • xanthone