Studies on the Alkaloids of Menispermaceous Plants. CCXLI. Synthesis of Cycleanine. (2). Bischler-Napieralski Reaction of N-Acyl-3, 4-dimethoxy-5-(4-substituted-phenoxy)-β-phenethylamines

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During the course of the studies for synthesis of II, the Ullmann reaction product of 8-bromoarmepavine, Bischler-Napieralski reaction of amide XI was carried out. Characterization of the product was effected by metallic sodium-liquid ammonia fission reaction. It was found that the isoquinoline ring-closure of such an amide formulated as XVIII occurred onto both o-and p-positions to the phenoxyl grouping, that is, the direction of the ring-closure was unexpectedly affected by substituent borne on 4-position of the phenoxyl grouping.