Synthesis of 4-(2-Fluoro-4-hydroxyphenyl)-1,2,3-thia- and -Selenadiazoles and Glycosides on Their Base

O. V. Stepanova, L. M. Pevzner, M. L. Petrov, N. P. Stepanova, N. B. Sokolova, A. V. Stepakov

Research output: Contribution to journalArticlepeer-review

Abstract

Basing on 2-fluoro-4-methoxyacetophenone 2-fluoro-4-hydroxyphenyl-1,2,3-thiadiazole was synthesized by means of the Hurd-Mori reaction. Under the conditions of phase transfer catalysis in water-chloroform system it was glycosylated with 1-α-bromo-2,3,4-tri-O-acetyl-D-xylopyranose. 2-Fluoro-4-hydroxy-1,2,3-selenadiazole can be prepared by oxidation of 2-fluoro-4-hydroxyacetophenone with selenium dioxide in acetic acid. Glycosylation of 2-fluoro-4-hydroxy-1,2,3-selenadiazole with 1-α-bromo-2,3,4,6-tetra-O-acetyl-D-galactopyranose leads to formation of corresponding glycoside. Alternative pathway for preparing of 1-β-[3-fluoro-4-(1,2,3-selenadiazol-4-yl)-phenyl]-2,3,4-tri-O-acetyl-D-xylopyranose including synthesis of 2-fluoro-4-hydroxyacetophenone xyloside and subsequent formation of selenadiazole ring was developed.
Original languageEnglish
Pages (from-to)1241-1248
Number of pages8
JournalRussian Journal of General Chemistry
Volume90
Issue number7
DOIs
StatePublished - Aug 2020

Keywords

  • Hurd–Mori reaction
  • 1,2,3-thiadiazole
  • 1,2,3-selenadiazole
  • glycosylation
  • aglycone
  • phase transfer catalysis

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