Premium
Synthesis and Chemistry of 4‐Aroyl‐3‐oxo‐ and 3‐Chloropyridazine Derivatives
Author(s) -
Shalaby Alyaa A.,
Youssef Ali M.,
Youssef Wael A.,
Shams Nabil A.
Publication year - 1994
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.199400063
Subject(s) - chemistry , computational chemistry , organic chemistry , combinatorial chemistry , medicinal chemistry
4H,5H‐6‐Phenyl (1a) and 6‐ p ‐phenoxyphenyl (1b) pyridazin‐3(2H)‐ones were reacted with aromatic aldehydes to give 4‐arylmethylpyridazm‐3(2H)‐ones (2a‐g), Oxidation of (2a‐g) with various oxidising agents (selenium dioxide in ethanol or chromium trioxide in acetic acid) gave 4‐aroyl‐6‐arylpyridazin‐3(2H)‐ones (3a‐g). Chlorination of (3a‐g) with phosphorous oxychloride afforded 4‐aroyl‐6‐aryl‐3‐chloropyridazine (4a‐g). 1H‐3‐Aryl‐5‐phenylpyrazolo[3,4‐c]pyridazines (5a‐d) were obtained by heating (4a‐d) with excess hydrazine hydrate. Hydroxyamination of (3e‐g) with iydroxylamine gave aryl‐4(6‐ p ‐phenoxyphenyl‐2,3‐dihydro‐3‐oxo)pyridazinyl oxime (6a‐c). Silylation of oximes (6b & 6c) gave (7a & 7b) as acyclic compound instead of the expected seven ‐ membered ‐ ring compound (8).