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Preparation of 5‐methyl‐2‐sulfanyl‐7 h ‐1,3,4‐thiadiazolo[3,2‐ a ]‐pyrimidin‐7‐ones
Author(s) -
Safarov Saifidin,
Kukaniev Muhamacho A.,
Karpuk Elena,
Meier Herbert
Publication year - 2007
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.5570440145
Subject(s) - chemistry , diketene , sulfanyl , ring (chemistry) , nucleophilic substitution , acylation , nucleophile , medicinal chemistry , dehydration , thiadiazoles , stereochemistry , organic chemistry , catalysis , biochemistry
7 H ‐1,3,4‐Thiadiazolo[3,2‐ a ]pyrimidin‐7‐ones can be prepared by the acylation of 5‐amino‐1,3,4‐thiadiazoles with diketene and subsequent ring closure (dehydration). Whereas arylthio substituents (SC 6 H 5 ) can be introduced in 2‐position by the replacement of Br, alkylthio groups (SC 2 H 5 ) have to be already presentin the starting 5‐amino‐1,3,4‐thiadiazole. The ambident nucleophile 2‐thiazolidinethione reacts in the Br substitution reaction on the N atom.