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Cyclic condensations of 2‐amino‐1,3,4‐thiadiazole with 1,3‐dicarbonyl compounds
Author(s) -
Lauer R. F.,
Zenchoff G.
Publication year - 1976
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.5570130218
Subject(s) - chemistry , ethyl acetoacetate , medicinal chemistry , stereochemistry , organic chemistry , catalysis
The reactions of 2‐amino‐1,3,4‐thiadiazole with 1,3‐dicarbonyl compounds are described. 2,4‐Pentanedione gave 2‐thiocyanato‐4,6‐dimethylpyrimidine while diethylmalonate and ethyl acetoacetate yielded 5‐hydroxy‐7 H ‐1,3,4‐thiadiazolo[3,2‐ a ]pyrimidin‐7‐one and 7‐methyl‐5 H ‐1,3,4‐thiadiazolo[3,2‐ a ]pyrimidin‐5‐one, respectively. The structure of the latter compound was confirmed by a synthesis of the alternative isomeric structure (5‐methyl‐7 H ‐1,3,4‐thiadiazolo[3,2‐ a ]pyrirnidin‐7‐one) from 2‐amino‐1,3,4‐thiadiazole and α‐bromocrotonic acid.