Acridone studies. III. The formation of aromatic hypobromites from the reaction of melicopine with bromine

Abstract

Evidence is presented that melicopine (1,2-dimethoxy-10-methyl-3,4-methyl-enedioxyacridone) reacts with bromine in methanol to yield a compound which is formulated as an aryl dihypobromite. Demethylation of the 1-methoxyl group occurs, followed by addition of bromine and methanol to the oxygenated ring. The reactions of this hypobromite are discussed, and several degradation products synthesized.