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Communication | Regular issue | Vol 6, No. 1, 1977, pp.37-41
Published online, 1st January, 1970
DOI: 10.3987/R-1977-01-0037
A Facile Formation of Benzo[a]quinolizin-4-ones

Tetsuji Kametani,* Hirofumi Terasawa, Masataka Ihara, and Keiichiro Fukumoto

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


Reaction of 3,4-dihydro-6,7-dimethoxy-1-methylisoquinoline (1) with diethyl α,γ-diethoxycarbonylglutaconate (2) in ethanol, followed by silica gel chromatography, gave 3-ethoxycarbonyl-6,7-dihydro-9,10-dimethoxybenzo[a]quinolizin-4-one (4). On the other hand, the above same reaction, followed by reduction with sodium borohydride, yielded 3-ethoxycarbonyl-2-diethoxycarbonylmethyl-1,2,3,6,7,11b-hexahydro-9,10-dimethoxybenzo[a]quinolizin-4-one (7). Hydrolysis of 4 and 7 with ethanolic potassium hydroxide furnished the same acid (6).