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.
- Hurd–Mori reaction
- phase transfer catalysis