Alkaloids of the Australian Rutaceae. The Structure and Reactions of Acronycidine

Abstract

Acronycidine, C₁₅H₁₅O₅N, is shown to be 4,6,7,8-tetramethoxyfurano-(2', 3'-2, 3)-quinoline (VI). It has been degraded to 2,4,5-trimethoxybenzoic acid by a series of reactions, one of which involves the conversion of 3-nitroso-5,7,8-trimethoxy-2,4-dihydroxyquinoline to 4,6,7-trimethoxyisatin by heating with mineral acid. This process appears to be of general application for the conversion of 2,4-dihydroxyquinolines to isatins. Acronycidine readily undergoes oxidative demethylation with either nitric or nitrous acid giving a 1,4-quinone. Quinones are likewise formed from several acronycidine derivatives.