イソヒノリン誘導体の合成研究 (第19報)
1-Phenyl-3-benzylisoquinolineの合成
1952 年 72 巻 9 号 p. 1087-1090
詳細
1952 年 72 巻 9 号 p. 1087-1090
As a preliminary examination of the physiological action of 6, 7-dimethoxy-3-benzyl-isoquinoline, 1-phenyl-3-benzylisoquinoline was prepared. Chalcone was chosen as the starting material and two methods were attempted. One was to lead it to α-methoxy- or α-hydroxy-β-benzamido-α, γ-diphenylpropane, followed by cyclization, and the other a cyclization of β-benzamido-α, γ-diphenylpropane, to 1-phenyl-3-benzyl-3, 4-dihydroisoquinoline which was dehydrogenated to the objective compound. The former method, lacking the alcoxyl group in the aromatic nucleus, failed to undergo isoquino-line cyclization although the reaction was carried out under fairy vigorous conditions and yielded an oxazoline derivative of m. p. 143-143.5°. The latter method yielded a syrupy isoquinoline compound which gave a platinate of m. p. 211-213° (decomp.). The latter clearly forms an isoquinoline compound as there is no fear of the formation of an oxazoline, and since the product differs from that obtained by the former method, it is seen that this method is not suitable.
