Studies of the selective O-alkylation and dealkylation of flavonoids. XII. A new, convenient method for synthesizing 3,5-dihydroxy-6,7-dimethoxyflavones from 3,5,6,7-tetramethoxyflavones.

Abstract

The 5-methoxy group on 3, 5, 6, 7-tetramethoxyflavones and the 3-methoxy group on 3, 6, 7-trimethoxy-5-tosyloxyflavones were selectively cleaved with anhydrous aluminum bromide in acetonitrile under controlled conditions without the cleavage of benzyloxy groups on the B ring. By the application of these reactions, seven 3, 5-dihydroxy-6, 7-dimethoxyflavones were easily synthesized from the corresponding 3, 5, 6, 7-tetramethoxyflavones which were synthesized from 3, 6-dihydroxy-2, 4-ω-trimethoxyacetophenone by means of the Allan-Robinson reaction followed by methylation.