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The structure of the diazonium coupling products of phenacyl thiocyanate and phenacyl selenocyanate with diazotized 3‐phenyl‐5‐aminopyrazole
Author(s) -
Farag Ahmad M.,
Fahmi Abdelgawad A.,
Abdelhamid Abdou O.,
Shawali Ahmad S.,
Algharib Mohamed S.
Publication year - 1987
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.5570240521
Subject(s) - chemistry , potassium thiocyanate , phenacyl , thiocyanate , phenacyl bromide , medicinal chemistry , benzoyl chloride , sodium thiocyanate , acetic anhydride , organic chemistry , catalysis
The reaction of diazotized 3‐phenyl‐5‐aminopyrazole with phenacyl thiocyanate 1a and phenacyl selenocyanate 1b afforded directly 2‐imino‐3‐(3‐phenyl‐5‐pyrazolyl)‐5‐benzoyl‐2,3‐dihydro‐1,3,4‐thiadiazole monohydrate 9a and 2‐imino‐3‐(3‐phenyl‐5‐pyrazolyl)‐5‐benzoyl‐2,3‐dihydro‐1,3,4‐selenadiazole monohydrate 9b , respectively. The products 9a and 9b were also obtained from the reaction of C ‐benzoyl‐ N ‐(3‐phenyl‐5‐pyrazolyl)formohydrazidoyl bromide 10 with potassium thiocyanate and potassium selenocyanate, respectively. Acetylation, benzoylation, and nitrosation of 9 afforded the corresponding diacetyl, dibenzoyl, and nitroso derivatives 11‐13 , respectively. Cyclization of C ‐benzoyl‐ N ‐(3‐phenyl‐5‐pyrazolyl)‐nitrilimine 6 was shown to give the pyrazolo [5,1‐ d ]triazole 8 and not the pyrazolo[5,1‐ c ]‐ as ‐triazine derivative 7 , as previously reported.