Studies on the Alkaloids of Menispermaceous Plants. CCXXV. : syntheses of Dauricine Type Bases.(2). : Synthesis of 2, 7-Bis(2-methyl-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinolin-1-ylmethyl)dibenzo-p-dioxin and Its Reductive Cleavage by Metallic Sodium in Liquid Ammonia

Abstract

The title compound, 2, 7-bis(2-methyl-6, 7-dimethoxy-1, 2, 3, 4-tetrahydroisoquinolin-1-ylmethyl)-dibenzo-p-dioxin (IX), was synthesized by the Bischler Napieralski reaction of N, N'-bis(3, 4-dimethoxyphenethyl) dibenzo-p-dioxin-2, 7-diacetamide (VI). This compound was identified with the non-phenolic product from the Ullmann condensation of dl-armepavine and dl-3'-bromo-4'-O-acetylarmepavine. Cleavage reaction of IX with sodium in liquid ammonia afforded dauricine-type bases (X and XI).