Post Graduate Teaching Department of Chemistry, Rashtrasant Tukadoji Maharaj Nagpur University, Nagpur-440 033, Maharashtra, India E-mail : spruhagharad@gmail.com, bnberad@gmail.com Manuscript received online 28 April 2015, revised 20 May 2015, accepted 22 May 2015 A series of quinoline based β-lactams (azetidinones) have been synthesized via cycloaddition reaction (Staudinger reaction) of imines with ketene. The methodology involves [2+2] cycloaddition of Schiff bases with chloroacetyl chloride in presence of triethylamine to yield the corresponding 1-arylamido-3-chloro-4-(2-chloroquinolin-3-yl)-azetidin-2-ones. The intermediate Schiff bases were synthesized by condensation of 2-chloroquinolin-3-carbaldehyde with various aroyl hydrazides in ethanol. The structures of final compounds have been confirmed on the basis of IR, 1H NMR, 13C NMR and mass spectral data. The synthesized compounds were screened for antibacterial activity against Gram-positive and Gram-negative bacteria by broth dilution method. Most of the compounds exhibited good to moderate activity against tested bacteria.