複素環式化合物の合成研究 第72報
イミダツォイソヒノリン誘導体の合成研究 その12 イミダツォイソヒノリン誘導体の閉環機構
1962 年 82 巻 7 号 p. 1063-1065
詳細
1962 年 82 巻 7 号 p. 1063-1065
Dehydrative cyclization of N-[(3, 4-dimethoxyphenethyl) carbamoylmethyl] benzamide or -furamide by the Bischler-Napieralski reaction results in dehydration from two molecules to form 3-phenyl- or 2-furyl-8, 9-dimethoxy-5, 6-dihydroimidazo [5, 1-a]-isoquinoline. In order to examine the reaction mechanism of this dehydrative cyclization, 1-benzoylaminomethyl- and 1-furamidomethyl-6, 7-dimethoxy-3, 4-dihydroisoquinolines and 1-(3, 4-dimethoxyphenethyl)-2-phenyl-2-imidazolin-5-one were synthesized and submitted to the same cyclization reaction from which the objective imidazo-isoquinoline derivatives were obtained. This has proved that the products obtained in the past by the cyclization of N-(3, 4-dimethoxyphenethyl)-2-acylamino-acetamides are not formed by monomolecular dehydration and that they are imidazoisoquinoline derivatives formed by bimolecular dehydration.
