Open AccessSynthesis and reactions of 4-(p-methoxybenzyl)-6-[5,6,7,8-tetrahydro-2-naphthyl]-pyridazin-3(2H-one
Author(s) -
Harb El-Din Nagwa
Publication year - 1999
Publication title -
journal of the serbian chemical society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.227
H-Index - 45
eISSN - 1820-7421
pISSN - 0352-5139
DOI - 10.2298/jsc9911663e
Subject(s) - piperidine , chemistry , acrylonitrile , morpholine , benzylamine , medicinal chemistry , aniline , yield (engineering) , thiourea , mannich base , pyridazine , base (topology) , organic chemistry , polymer , mathematics , mathematical analysis , materials science , copolymer , metallurgy
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.