Synthetic and Mechanistic Investigations in cis-3-(Substituted acetoxy)azetidin-2-ones from cis-3-Hydroxyazetidin-2-ones: Potential Synthons for Pharmacophoric Hybridized Molecules

The present work describes the synthesis of cis-3-(substituted acetoxy)azetidin-2-ones from cis-3-hydroxyazetidin-2-ones. Two different routes have been investigated for the substitution at the C-3 position of the azetidin-2-ones. Method A involves the use of acetyl chloride XCOCl in the presence of pyridine and method B consists of using appropriate acid XCOOH in a catalytic amount of DMAP which was found to be the best to furnish the target azetidin-2-one. All the newly synthesized compounds were characterized on the basis of various spectroscopic techniques (FT-IR, H-1 NMR, C-13 NMR, and elemental analysis). Two different routes have been investigated for the substitution at the C-3 position of the azetidin-2-ones.