98260-81-2Relevant academic research and scientific papers
THE SYNTHESIS OF 2,3,7,8-BISMETHYLENEDIOXY-11-METHOXY-5-METHYLBENZOPHENANTHRIDINIUM CHLORIDE
Smidrkal, Jan,Holubek, Jiri,Trojanek, Jan
, p. 984 - 990 (2007/10/02)
Acylation of 3-methoxy-6,7-methylenedioxy-1-methylaminonaphthalene (VI) with 6-bromo-2,3-methylenedioxybenzoyl chloride gave N-(3-methoxy-6,7-methylenedioxynaphth-1-yl)-N-methylamide of 6-bromo-2,3-methylenedioxybenzoic acid (IIIa) the irradiation of which with ultraviolet light in acetonitrile and triethylamine gave N-methyl-2,3-methylenedioxy-1-(3'-methoxy-6',7'-methylenedioxynaphth-1-yl)benzamide (Xa) in low yield in addition to 2,3,7,8-bismethylenedioxy-11-methoxy-5-methyl-6-oxobenzophenanthridine (Va).The last compound was converted to dihydro derivative VIa from which 2,3,7,8-bismethylenedioxy-11-methoxy-5-methylbenzo-phenanthridinium chloride (Ia) was prepared.Chloride Ia differs from the alkaloid chelirubine (IIa) to which the structure Ia was assigned originally.Under analogous conditions irradiation of N-(3-methoxy-6,7-methylenedioxynaphth-1-yl)-N-methylamide of 6-bromo-2,3-dimethoxybenzoic acid (IIIb) leads to debrominated starting amide XIIIb on the one hand and to N-methyl-2,3-dimethoxy-1-(3'-methoxy-6',7'-methylenedioxynaphth-1-yl)benzamide (Xb) on the other.The expected phenanthridone derivative Vb could not be detected in the reaction mixture.
