New chalcones (3a-h) were synthesized from 2-chloro-8-methoxy-quinoline-3-carbaldehyde (2) and halohydroxysubstitued acetophenones (1a-h) via Claisen-Schmidt condensation. Further new flavones (4a-h) were synthesized by oxidative cyclisation of chalcones (3a-h) using microwave as well as by conventional method. The structures of synthetic compounds were established on the basis of analytical and spectral data. These compounds were screened for their antibacterial activity.