1953 年 73 巻 7 号 p. 681-685
In order to examine whether rearrangement of the double bond occurred in isoquinoline derivatives, α-veratryl-γ-piperonyl-and α-piperonyl-γ-veratryl-β-benzamidopropane were prepared and isoquinoline cyclization with phosphoryl chloride carried out on them. The latter substance yielded two kinds of products one of which was found to be identical with the cyclization product of the former, there being no depression of the melting point on admixture and showing identical infrared absorption spectra. The other substance obtained from the latter was crystals of m.p. 180-183° which showed notable difference in the absorption range of double bonds and in a longer wave length range. It follows, therefore, that an identical substance had been obtained by the isoquinoline cyclization of the foregoing two kinds of acid amides as a consequence of the migration of the double bond. However, the cyclizable two aromatic rings in the acid amides both possess alkoxyl groups that the formation of two kinds of compounds can be expected and no definite confirmations can be made as to their structures. Further studies are being made on this point.