Dirhodium(II) tetraacetate catalysed reactions of diazo thioamides: isolation and cycloaddition of anhydro-4-hydroxy-1,3-thiazolium hydroxides (thioisomunchnones), an approach to analogues of dehydrogliotoxin

CJ Moody, Alexandra Martha Zoya Slawin, D Willows

Research output: Other contribution

24 Citations (Scopus)

Abstract

Dirhodium(II) tetraacetate catalysed reaction of the indoline diazo thioamide 8 gives the thioisomunchnone 9, a stable characterisable solid. This masked thiocarbonyl ylide undergoes 1,3- dipolar cycloaddition with N-methylmaleimide and maleic anhydride to give the exo-cycloadducts 10 and 11, characterised by X-ray crystallography. The thioisomunchnone 18, derived from diazo thioamide 17, is an extremely stable crystalline mesoionic system which can be characterised by X-ray crystallography but fails to undergo intramolecular cycloaddition. The related thioisomunchnone 19 can be generated by reaction of indoline-2-thione 7 with bromoacetyl chloride in the presence of triethylamine, and undergoes cycloaddition to give adducts 20 and 21.

Original languageEnglish
Volume1
DOIs
Publication statusPublished - 2003

Keywords

  • MESOIONIC COMPOUNDS
  • ANHYDRO-4-HYDROXYTHIAZOLIUM HYDROXIDE
  • CYCLIZATION
  • SYSTEMS
  • DIPOLAROPHILES
  • HETEROCYCLES
  • GENERATION
  • GLIOTOXIN
  • CHEMISTRY

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