Synthesis of Novel cis-2-Azetidinones from Imines and Chloroacetyl Chloride Using Triethylamine

Abstract

A synthesis of a novel series of cis-2-azetidinones 2a-c was carried out by the cycloaddition reaction of imine 1a-c and chloroacetyl chloride in dry dichloromethane at 0-5°C using triethylamine. The cycloaddition of the Schiff bases with chloroacetyl chloride resulted in the corresponding major product cis-2-azetidinone stereoisomers 2a-c. The synthesized compounds were characterized by analytical and spectral techniques (infrared, 1H NMR, 13C NMR, and elemental analysis).