3-Methyl-4-(arylbenzylideneamino)-(aryl)methyl)-1-phenyl-1H-pyrazol-5-(4H)-one has been prepared by the reaction of 3-methyl-1H-pyrazol-5(4H)-one, aldehydes and ammonia via Betti’s condensation reaction, which on further treatment with chloroacetic acid and POCl3 in the presence of triethylamine gave the 4-((3-chloro-2-(aryl)- 4-oxoazetidin-1-yl)(aryl)-methyl)-3-methyl-1-phenyl-1H-pyrazol-5(4H)-one. The structures of the compounds were confirmed by using different spectroscopic techniques (IR and 1H-NMR) and elemental analysis. These azetidinones analogues were screened for their antimicrobial activities against strains of different microorganisms. Some of the compounds displayed the promising antibacterial activities against some bacterial strains.