Convenient synthesis of 1,6,7,8-substituted 2-(3′,4′-substituted-phenyl)-4-quinolones via a 4-ethoxyflavylium salt

Condensation of 2-hydroxyacetophenone with benzaldehyde in the presence of 70% perchloric acid in ethyl orthoformate gave the corresponding 4-ethoxyflavylium perchlorate, which was treated with aqueous ammonia or methylamine solution to afford 1,6,7,8-substituted 2-(3′,4′-substituted-phenyl)-4-quinolone in fair to good yield.