T. Kametani, K. Kigasawa, M. Hiiragi
Dec 1, 1973
Citations
0
Influential Citations
3
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
1,2,3,4,5,6-Hexahydro-8-hydroxy-2,6-methano-3,6,1 1-trimethyl-2,3-benzo |g| diazocine (IV) and 1,2,3,4,5,10,11,12-octahydro-7-hydroxy-1,5-dimethylpyridazino |2,3-b| isoquinoline (VI) were synthesized from a common intermediate, 3-(3-methoxyphenyl)-2-butanone (VII), through several steps. Reaction of VII with ethyl bromoacetate gave the mixture of ethyl 4-keto-3-(3-methoxyphenyl)-3-methylpentanoate (XIV) and ethyl 4-keto-5-(3-methoxyphenyl)hexanoate (XV) which were hydrolyzed and condensed with methylhydrazine to give the 4,5-dihydro-5-(3-methoxyphenyl)-2,5,6-trimethyl- (XVIII) and 4,5-dihydro-6-(3-methoxy-α-methylbenzyl)-2-methylpyridazine-3(2H)one (XIX). Reduction of XVIII and XIX followed hy cyclization afforded the 2,3-benzo |g| diazocine (XXII) and the pyridazino |2,3-b| isoquinoline (XXIII) which on treatment with 47% hydrobromine acid afforded the phenolic bases (IV and VI), respectively. The mass spectrum of IV, VI, XXII and XXIII was also discussed.