Synthesis and reactions of 4-(p-methoxybenzyl)-6-[5,6,7,8-tetrahydro-2-naphthyl]-pyridazin-3(2H-one

• Main Author: El-Din Harb Nagwa M.S.
• Format: Article
• Language: English
• Published: Serbian Chemical Society 1999-01-01
• Series: Journal of the Serbian Chemical Society
• Subjects: pyridazin-3(2h)-one; dimethyl sulphate; formaldehyde; acrylonitrile; chlo-ropyridazine; benzylamine; aniline; piperidine; pyridazinthione; morpholine
• Online Access: http://www.doiserbia.nb.rs/img/doi/0352-5139/1999/0352-51399911663E.pdf

The condensation of 4-(p-methoxybenzyl)-6-[5,6,7,8-tetrahydro-2-naphthyl]- pyridazin-3(2H)-one (3), prepared by the reaction of 6-[5,6,7,8-tetrahydro-2-naphthyl]-4,5-dihydropyridazin-3(2H)-one (1) and anisaldehyde, with dimethyl sulphate, formal-dehyde and acrylonitrile, and also the formation of the Mannich base, proceeded smoothly at the 2-position to give compounds 4,5,6,7, respectively. 4-p-Methoxybenzyl-3-chloro-6-[5,6,7,8-tetrahydro-2-naphthyl]-pyridazine (9) was prepared in law yield by the action of phosphorus oxychloride on 3. The reaction of 9 with benzylamine, aniline and piperidine gave 10a,b,c, respectively. 4-p-Methoxybenzyl-6-[5,6,7,8-tetrahydro-2-napthyl]pyridazine-3(2H)-thione (12) was prepared either by the action of thiourea on 9, or by the reaction of 3 with phosphorus pentasulphide. The reaction of these thiones with acrylonitrile, morpholine and piperidine to give 13 and 14 a,b, respectively, were also investigated.