Polymethoxylated 4-aryl-2-quinolones were synthesized from the corresponding (o-aminophenyl)propiolates via Cu-catalyzed hydroarylation and subsequent deprotection/lactam formation. Selective iodination of the C3 position of the product followed by coupling reactions of the resulting 3-iodinated 4-aryl-2-quinolone afforded 3-substituted-4-aryl-2-quinolones. Moreover, the N-benzyl protecting group was successfully replaced with other polyoxygenated benzyl groups.