Collect. Czech. Chem. Commun. 1979, 44, 1334-1338

Synthesis of 3,5-disubstituted 1,2,4-triazole derivatives - An alternative preparation of the C-analogue of ribavirin

Tomáš Vaněk, Jiří Farkaš and Jiří Gut

Institute of Organic Chemistry and Biochemistry, Czechoslovak Academy of Sciences, 166 10 Prague 6


Condensation of ethyl acetothioimidate hydrochloride (III) with amidrazones IV afforded 3-methyl-5-phenyl-1,2,4-triazole (Va) and ethyl 3-methyl-1,2,4-triazole-5-carboxylate (Vb). Analogously, the thioimidate hydrochloride VI was transformed into ethyl 5-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-1,2,4-triazole-3-carboxylate (VIIa) which, after removal of benzoyl groups, was ammonolysed to the amide II.