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Synthesis of 2‐(2′,3′‐dihydroxypropyl)‐5‐amino‐2 H ‐1,2,4‐thiadiazol‐3‐one and 3‐(2′,3′‐dihydroxypropyl)‐5‐amino‐3 H ‐1,3,4‐thiadiazol‐2‐one
Author(s) -
Párkányi Cyril,
Yuan Hui Liang,
Cho Nam Sook,
Jaw JinHwa J.,
Woodhouse Tamar E.,
Aung Thomas L.
Publication year - 1989
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.5570260520
Subject(s) - chemistry , dimethylformamide , anhydrous , stereochemistry , salt (chemistry) , condensation , triethylamine , medicinal chemistry , organic chemistry , physics , solvent , thermodynamics
The synthesis of two new acyclic nucleoside analogs, 2‐(2′,3′‐dihydroxypropyl)‐5‐amino‐2 H ‐1,2,4‐thiadiazol‐3‐one (1) and 3‐(2′,3′‐dihydroxypropyl)‐5‐amino‐3 H ‐1,3,4‐thiadiazol‐2‐one (2), is reported. The first compound, 1, was obtained by reaction of 3‐chloro‐1,2‐propanediol with the sodium salt of 5‐amino‐2 H ‐1,2,4‐thiadiazol‐3‐one (3) in anhydrous dimethylformamide. Similarly, 5‐amino‐3 H ‐1,3,4‐thiadiazol‐2‐one (4) reacted with 3‐chloro‐1,2‐propanediol to give 2. The thiadiazole 4 was prepared by condensation‐cyclization of hydrazothiodicarbonamide (9).