1959 年 79 巻 10 号 p. 1314-1318
In order to find synthetic anti-ameba agent, hydrogenated benzoquinolizines (A) with basic side chain of -(CH2)nN(CH3)2 type were prepared. The quaternary salt (I), obtained from nicotine monohydrochloride and 2, 4-dimethoxyphenethyl bromide, was oxidized to the pyridone (II), hydrogenated to the piperidone (III), and submitted to the Hofmann degradation to the methine base, which was fouud to have the formula (IV) from optical rotation, infrared spectrum, and behavior of its methiodide to oxidation with potassium permanganate or ozone. The second Hofmann degradation of (IV) was carried out to confirm the presence of trimethylamine and a butadiene compound (VI) was obtained. The permanganate oxidation of its butene compound (VIII) to the compound (IX) with carboxymethyl side chain, and its cyclization and reduction afforded the quinolizine ester (X). From its amide (XI), the amide (XIII) of (A) type with n=2 was obtained. Cyclization of the hydrogenated product (XIV) of (IV) with phosphoryl chloride afforded the amine (XV) of (A) type with n=4. The Hofmann degradation of (XIV) afforded an unsaturated neutral substance (XVI) whose structure was also confirmed. Oxidation of (XVI) with potassium permanganate gave a compound with -(CH2)2-COOH side chain and an amine (XX) of (A) type with n=3 was obtained from it by the same procedure as with (IX).