Synthesis of 1,2,3‐triazole nucleosides via the acid‐catalyzed fusion procedure

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Abstract
The acid‐catalyzed fusion of methyl 1,2,3‐triazole‐4‐carboxylate, 4‐cyano‐1,2,3‐triazole, and 4‐nitro‐1,2,3‐triazole with an acylated ribofuranose provided the corresponding 2‐β‐D‐ribo‐furanosyl‐4‐substituted‐1,2,3‐triazoles along with the isomeric 1‐β‐D‐ribofuranosyl‐4‐substituted‐1,2,3‐triazoles. The structures of these nucleosides were assigned on the basis of their nmr spectra. The synthesis of 2‐β‐D‐ribofuranosyl‐1,2,3‐triazole‐4‐carboxamide from both the corresponding methyl ester and cyano nucleosides is described. The cyano nucleosides were utilized to prepare 2‐β‐D‐ribofuranosyl‐1,2,3‐triazole‐4‐thiocarboxaḿide and 1‐β‐D‐ribofuranosyl‐1,2,3‐triazole‐4‐thiocarboxamide. Reduction of the 4‐nitro‐1,2,3‐triazole nucleosides provided 4‐amino‐2‐β‐D‐ribofuranosyl‐1,2,3‐triazole and the isomeric 4‐amino‐1‐β‐D‐ribofuranosyl‐1,2,3‐triazole. The acid‐catalyzed fusion procedure with 1,2,3‐triazole afforded 1‐β‐D‐ribofuranosyl‐1,2,3‐triazole and 2‐β‐D‐ribofuranosyl‐1,2,3‐triazole.