A new approach to the synthesis of nucleosides of 1,2,4-triazole

Abstract

Reaction of benzamidrazone hydroiodide 1 with D-glucose 2, D-galactose 3 and D-arabinose 8 followed by acetylation afforded 1-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-, 1-(2,3,5,6-tetra-O-acetyl-α-D-galactofuranosyl)- and 1-(1,2,3,4,5-penta-O-acetyl-D-manno-pentitol-1-yl)-5-methyl-3-phenyl-1H-1,2,4-triazole 6, 7 and 13, respectively. Structural analyses of these products were carried out by ¹H, ¹³C, and 2D NMR spectra (DQFCOSY, HMQC and HMBC experiments), as well as by MS, FABMS and X-ray crystallography.