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Synthesis of nucleosides of 5‐substituted‐1,2,4‐triazole‐3‐carboxamides
Author(s) -
Naik S. R.,
Witkowski J. T.,
Robins Roland K.
Publication year - 1974
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570110112
Subject(s) - carboxamide , chemistry , 1,2,4 triazole , triazole , 1,2,3 triazole , stereochemistry , medicinal chemistry , organic chemistry
Nucleosides of 5‐substituted‐1,2,4‐triazole‐3‐carboxamides were prepared by the acid‐catalyzed fusion procedure and by glycosylation of the appropriate trimethylsilyl derivative. The following nucleosides were obtained in two steps starting from methyl 4‐substituted‐1,2,4‐triazole‐3‐carboxylates: 5‐chloro‐1‐β‐ D ‐ribofuranosyl‐1,2,4‐triazole‐3‐carboxamide ( 6 ), 3‐chloro‐1‐β‐ D ‐ribofuranosyl‐1,2,4‐triazole‐5‐carboxamide ( 5 ), 3‐nitro‐1‐β‐ D ‐ribofuranosyl‐1,2,4‐triazole‐5‐carboxamide ( 12 ), 3‐amino‐1‐β‐ D ‐ribofuranosyl‐1,2,4‐triazole‐5‐carboxamide ( 13 ), 5‐methyl‐1‐β‐ D ‐ribofuranosyl‐1,2,4‐triazole‐3‐carboxamide ( 15 ), and 3‐methyl‐1‐β‐ D ‐ribofuranosyl‐1,2,4‐triazole‐5‐carboxamide ( 16 ). In addition, 5‐amino‐1‐β‐ D ‐ribofuranosyl‐1,2,4‐triazole‐3‐carboxamide ( 7 ), and 1‐β‐ D ‐ribofuranosyl‐1,2,4‐triazole‐3‐carboxamide‐5‐thiol ( 8 ) were prepared from 6 .