Synthesis of some heterocyclic systems of anticipated biological activities via 6-aryl-4-pyrazol-1-yl-pyridazin-3-one

• Published in: Canadian journal of chemistry Vol. 83; no. 3; pp. 251 - 259
• Main Authors: Youssef, A SA, Marzouk, M I, Madkour, H MF, El-Soll, A MA, El-Hashash, M A
• Format: Journal Article
• Language: English
• Published: Ottawa, Canada NRC Research Press 01.03.2005; Canadian Science Publishing; Canadian Science Publishing NRC Research Press
• Subjects: Chemical compounds; Chemical reactions; Chemistry; Chemistry, Multidisciplinary; Esters; Physical Sciences; Science & Technology; 3,6-diaryl-1,2,4triazino[-4,3-b] pyridazine derivative; ACETYLENIC KETONES; 6-aryl-3-ethoxycarbonylmethoxypyridazine derivative; 6-aryl-3-chloropyridazine derivative; 6-aryl-4-pyrazol-1-yl-pyridazinone derivative; 6-aryl-3-(omega-benzoylacetophenone)hydrazinocarbonylmethoxypyridazine
• ISSN: 0008-4042; 1480-3291
• DOI: 10.1139/v05-045

6-Aryl-4-pyrazol-1-yl-pyridazin-3-one ( 1 ) reacted with a PCl 5 –POCl 3 mixture to give the 3-chloropyridazine derivative 3 . Reaction of 3 with 2-hydroxybenzoylhydrazide and semicarbazide hydrochloride afforded 4 and 5 . Reaction of 1 with ethyl chloroacetate gave 8 . Reaction of 8 with hydrazine hydrate yielded the hydrazide 9 . The hydrazide 9 condensed with the acetylenic ketones and esters 10a – 10d and acetylacetone to give the adducts 11a , 11b , 12 , 13 , and 14 . Reacting 1 with formaldehyde and piperidine, morpholine, or piperazine, 3-bromopropanoic acid, acetic anhydride, p-toluenesulphonyl chloride, succinyl chloride, oxalyl chloride, ethanolamine, or ethyl chloroacetate gave the adducts 15 – 22 . The structures of all newly synthesized compounds were evidenced from their spectral and microanalytical data. Key words: 6-aryl-4-pyrazol-1-yl-pyridazinone derivative, 6-aryl-3-chloropyridazine derivative, 3,6-diaryl-1,2,4-triazino[4,3-b]pyridazine derivative, 6-aryl-3-ethoxycarbonylmethoxypyridazine derivative, 6-aryl-3-(ω-benzoylacetophenone)hydrazinocarbonylmethoxypyridazine.