Resorcinol based bis-chalcones (2a-d) and flavones (3a-d) were synthesized and evaluated for their antimicrobial activity. Bis-chalcones (2a-d) were prepared by condensing 1,1´-(4,6-dihydroxy-1,3-phenylene)diethanone (1) with appropriate aryl-aldehydes, oxidative cyclization of bis-chalcones in presence of iodine gave corresponding flavones (3a-d). The synthesized compounds were evaluated for their antimicrobial actions against some selected bacterial and fungal strains. One compound, 1-{2,4-dihydroxy-5-[3-(2,4-dichlorophenyl)-2-propenoyl]phenyl}-3- (2,4-dichlorophenyl)-2-propen-1-one (2d), emerged as lead compound with significant antimicrobial activities.