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

• Published in: Journal of the Chinese Chemical Society (Taipei) 2008-08, Vol.55 (4), p.834-841
• Main Authors: Zhang, Huan‐Huan, Hu, Xiu‐Qin, Fan, Gui‐Fang, Xu, Peng‐Fei
• Format: Article
• Language: English
• ISSN: 0009-4536; 2192-6549
• DOI: 10.1002/jccs.200800124

The synthesis of some new S‐nucleosides of 5‐(4‐pyridyl)‐4‐aryl‐4 H ‐1,2,4‐triazole‐3‐thiols ( 4a‐n ) is described. Direct glycosylation of ( 4a‐n ) with tetra‐ O ‐acetyl‐α‐D‐glucopyranosyl bromide in the presence of potassium hydroxide followed by deacetylation using dry ammonia in methanol gave the corresponding 3‐S‐(ñ‐D‐glucopyranosyl)‐5‐(4‐pyridyl)‐4‐aryl‐4 H ‐1,2,4‐triazoles ( 6a‐n ) in good yields. All the compounds were fully characterized by means of 1 HNMR, 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‐ O ‐acetyl‐β‐D‐glucopyranosyl)‐5‐(4‐pyridyl)‐4‐phenyl‐4 H ‐1,2,4‐triazole ( 5a ) was determined by X‐ray diffraction. 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 1H NMR, 13C 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‐O‐acetyl‐b‐D‐glucopyranosyl)‐5‐(4‐pyridyl)‐4‐phenyl‐4H‐1,2,4‐triazole (5a) was determined by X‐ray diffraction.