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Synthesis and characterization of 3-phenylthio/3-phenoxyazetidine-2-one: Application of two dimensional NMR HMQC 1H-13C, COSY 1H–1H and mass spectroscopy

Mahmood Shakir Magtoof, Z.S.Hassan, Kasim Mohammed Hello

A series of cis and trans 3–phenylthio/3-phenoxyazetidine-2-one (3a-e) have been synthesized via Schiff bases (2a-d) in the presence of triethylamine with phosphorusoxychloride using dry methylene chloride under nitrogen atmosphere at 0C. The active acid chloride reacts with triethylamine to generate corresponding ketene in situ which further react with Schiff’s base to furnish the corresponding cis and trans 3–phenylthio/3- phenoxyazetidine-2-one (3a-e) in moderate yields. The calculated and the found values of Carbon, Hydrogen, and Nitrogen percentage in the elemental analysis were in agreement with each other. The mass spectroscopy confirms themolecularweight of the prepared compound. Furthermore, the two dimensionalNMRHMQC1H-13C,COSY1H–1Hwas used to confirmthe proposed structure and the stereochemistry of the synthesized compound.