Synthesis of 2-pyranosyl benzothiazoles, benzimidazoles and benzoxazoles via nucleophilic addition reactions of pyranosyl nitrile oxides

Iain A. S. Smellie, Andreas Fromm, Francesca P. A. Fabbiani, Iain D. H. Oswald, Fraser J. White, R. Michael Paton

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Abstract

Reaction of per-O-acetylated-beta-D-pyranosyl nitrile oxides, generated by dehydrochlorination of the corresponding hydroximoyl chlorides, with 2-aminothiophenol afforded 2-(beta-D-pyranosyl)benzothiazoles. 1,2-Diaminobenzene and 2-aminophenol reacted similarly to yield 2-(beta-D-pyranosyl)benzimidazoles and 2-(beta-D-pyranosyl)benzoxazoles, respectively. The structures of 2-beta-D-glucopyranosylbenzimidazole (17), 2-(2,3,4-tri-O-acetyl-beta-D-xylopyranosyl)benzimidazole (19) and the xylopyranosyl thiohydroximate 13 were established by X-ray crystallography. (C) 2010 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)7155-7160
Number of pages6
JournalTetrahedron
Volume66
Issue number35
DOIs
Publication statusPublished - 28 Aug 2010

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Keywords

  • Nitrile oxides
  • C-Glycosides
  • Pyranosyl benzimidazoles
  • Pyranosyl benzoxazoles
  • Pyranosyl benzothiazoles
  • X-ray crystallography
  • clycogen-phosphorylase inhibitors
  • C-Nucleosides
  • cycloaddition reactions
  • glycosyl
  • sugar
  • heterocycles
  • derivatives
  • chemistry
  • chlorides
  • cyanides

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