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Communication | Regular issue | Vol 4, No. 5, 1976, pp.921-926
Published online, 1st January, 1970
DOI: 10.3987/R-1976-05-0921
A New Alkylating Method at the 4-Position of Isoquinoline Deivatives

Tetsuji Kametani,* Hideo Nemoto, Mie Takeuchi, Mitsuhiro Takeshita, and Keiichiro Fukumoto

*Pharmaceutical Institute, Tohoku University, Aobayama, Sendai 980-8578, Japan


Alkylation of 3,4-dihydro-6,7-dimethoxy-1-methylisoquinoline (I) with 2-methylcyclohex-2-en-1-one and phenethyl bromide in the presence of sodium hydride and dimethyl sulphoxide gave 6,7-dimethoxy-1-methyl-4-(2-methyl-3-oxocyclohexyl)isoquinoline (V) and 6,7-dimethoxy-1-methyl-4-phenethylisoquinoline (VII), respectively. On the other hand, reaction of 3,4-dihydro- 6,7-dimethoxyisoquinoline (VIII) with 3,4-methylenedioxyphenethyl bromide under the same conditions gave 6,7-dimethoxy-1-methylisoquinoline (XI) and methyl 3-(3,4-methylenedioxyphenyl)propyl sulphoxide (XII).