A straightforward rapid and efficient protocol for the synthesis of 2-azetidinone (D1-10) and 5-benzylidine-4-oxo-thiazolidine (F1-10) has been designed and synthesized in order to find newer antimicrobial compounds. The structure of entitle compounds have been evaluated on the basis of various spectroscopic techniques FTIR, 1H-NMR, 13C-NMR as well as elemental microanalysis. The title compounds were screened for their preliminary in vitro antibacterial activity against a panel of selected pathogenic bacterial strains, Staphylococcus aureus (MTCC 96), Escherichia coli (MTCC 443), Proteus vulgaris (MTCC 426) and Pseudomonas aeruginosa (MTCC 424) using cup-plate agar diffusion method at 40 μg/ml concentration. Out of synthesized compounds, compound nos. D4, D5, D7, D8, D9 and D10 have shown outstanding inhibitory effect against all pathogens and consider as the best bioactive desired antibacterial analogue of the series as compare to standard drugs ampicilline and chloramphenicol.