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Heterocycles from Pyrazoloylhydroximoyl Chloride: Synthesis of Certain Quinoxaline, Benzothiadiazine, Benzoxadiazine, Quinazolinone, Imidazo[1,2‐ a ]pyridine, Imidazo[1,2‐ a ]pyrimidine, Isoxazole, Pyrazolo[3,4‐ d ]pyridazine and Pyrrolidino[3,4‐ d ]isoxazolin‐4,6‐dione Derivatives
Author(s) -
Zohdi Hussein F.,
Osman Tabia A.,
Abdelhamid Abdou O.
Publication year - 1997
Publication title -
journal of the chinese chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.329
H-Index - 45
eISSN - 2192-6549
pISSN - 0009-4536
DOI - 10.1002/jccs.199700095
Subject(s) - chemistry , isoxazole , benzothiadiazine , pyridine , quinazolinone , quinoxaline , methylene , pyrimidine , medicinal chemistry , chloride , benzoyl chloride , organic chemistry , stereochemistry
3‐Ethoxycarbonyl‐5‐methyl‐1‐(4‐methylphenyl)‐4‐pyrazoloylhydroximoyl chloride (1) reacted with o ‐phenylenediamine, o ‐aminothiophenol, o ‐aminophenol and methyl anthranilate to afford 3‐nitrosoquinoxaline, benzothiadiazine, benzoxadiazine, and 3‐hydroxyquinazoline, respectively. Imidazo[1,2‐ a ]pyridine, imidazo[1,2‐ a ]pyrimidine and isoxazole derivatives were obtained via the reaction of 1 with 2‐aminopyridine, 2‐aminopyrimidine and the appropriate active methylene compounds, respectively. Pyrazolo[3,4‐ d ]pyridazines, and pyrrolidino[3,4‐ d ]isoxazolines derivatives were also synthesized. The structures of the newly synthesized compounds were established on the basis of spectral data and alternate synthesis whenever possible.