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Synthesis of Antipyrine Derivatives Derived from Dimedone
Author(s) -
Ei ashry E. S. H.,
Awad L. F.,
Ibrahim E. I.,
Bdeewy O. Kh.
Publication year - 2007
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.200790107
Subject(s) - chemistry , dimedone , phenylhydrazine , acetic anhydride , hydroxylamine , derivative (finance) , hydroxylamine hydrochloride , hydrochloride , pyridine , organic chemistry , medicinal chemistry , catalysis , financial economics , economics
Abstract Coupling of dimedone with the diazonium salt of 4‐aminoantipyrine afforded 2,3‐dimethyl‐4‐[2‐(5,5‐dimethyl‐ 2,6‐dioxocyclohex‐2‐ylidend)‐hydrazino]‐5‐oxo‐1‐phenylpyrazoline ( 3 ). Reaction of 3 with excess phenylhydrazine gave the mixed trishydrazone derivative 4 . Treatment of 3 with hydroxylamine produced the bisoxime 5 which upon dehydrative cyclization with acetic anhydride gave the corrsponding tetrahydrobenzo[d][1,2,3]triazole derivative 7 . A one‐pot synthesis of 7 was done by reacting 3 with hydroxylamine hydrochloride in pyridine, followed by heatment with acetic anhydride.