Synthesis and Molecular Structure of New S‐Nucleosides of 5‐(4‐Pyridyl)‐4‐Aryl‐4H‐1,2,4‐Triazole‐3‐Thiols

Abstract

The synthesis of some new S-nucleosides of 5-(4-pyridyl)-4-aryl-4H-1,2,4-triazole-3-thiols (4a-n) is described. Direct glycosylation of (4a-n) with tetra-O-acetyl-a-D-glucopyranosyl bromide in the presence of potassium hydroxide followed by deacetylation using dry ammonia in methanol gave the corresponding 3-S-(b-D-glucopyranosyl)-5-(4-pyridyl)-4-aryl-4H-1,2,4-triazoles (6a-n) in good yields. All the compounds were fully characterized by means of 1 H NMR, 13 C NMR spectra and elemental analyses. To assist in the interpretation of the spectroscopic data, the crystal structure of 3-S-(2¢,3¢,4¢,6¢-tetra-Oacetyl-b-D-glucopyranosyl)-5-(4-pyridyl)-4-phenyl-4H-1,2,4-triazole (5a) was determined by X-ray diffraction.