Studies on the Alkaloids of Menispermaceous Plants. CLXII

Reaction of Isotetrandrine Dimethiodide by Metallic Sodium in Liquid Ammonia

Abstract

Cleavage reaction of isotetrandrine dimethiodide (VI), a quaternary base of the biscoclaurine type, with liquid ammonia and sodium was examined. As a result, N, N-dimethylcoclaurine hydromethine (VII) was identified as the phenolic base. The nonphenolic base was examined by paper chromatography and it was found to be a mixture of several decomposed bases, which could not be isolated into each unity. From the Rf values, however, the presence of N, O-dimethylarmepavine hydromethine (V) was assumed. It follows that in this reaction, Emde decomposition occurs besides the ordinary cleavage of the ether oxygen forming the diphenyl ether linkage and the base is decomposed to the methyl hydromethine stage.