Premium
On the preparation of substituted 4 H‐ 1,3,4‐thiadiazolo[2,3‐ c ]‐1,2,4‐triazin‐4‐ones and 1,2,4‐triazolo[3,4‐ b ]‐1,3,4‐thiadiazoles
Author(s) -
Coppo Frank T.,
Fawzi Maged M.
Publication year - 1997
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.5570340443
Subject(s) - chemistry , trifluoromethyl , thiourea , isothiocyanate , acetonitrile , benzamide , medicinal chemistry , triazole , bicyclic molecule , phenyl isothiocyanate , stereochemistry , organic chemistry , alkyl
The reaction of benzoyl isothiocyanates and methoxycarbonyl isothiocyanate with 4‐amino‐4,5‐dihydro‐3‐(methylthio)‐1,2,4‐triazin‐5‐ones in acetonitrile gave several substituted 4 H ‐1,3,4‐thiadiazolo[2,3‐ c ]‐1,2,4‐triazin‐4‐ones VIa‐h instead of the expected thioureas. In addition, benzoyl isothiocyanate reacted with 4‐amino‐3‐(methylthio)‐5‐(trifluoromethyl)‐4 H ‐1,2,4‐triazole to give the benzoyl thiourea IX and with 4‐amino‐3‐mercapto‐5‐(trifluoromethyl)‐4 H ‐1,2,4‐triazole to give the bicyclic compound N ‐[3‐(trifluoromethyl)‐1,2,4‐triazolo[3,4‐b]‐1,3,4‐thiadiazol‐6‐yl]benzamide IX .