Synthesis, characterization and antibacterial study of 1-arylamido-3-chloro-4- (2-chloroquinolin-3-yl)-azetidin-2-ones

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.