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Letters in Organic Chemistry

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ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

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Research Article

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

Author(s): Aman Bhalla*, Garima Modi, Jaswinder Kaur, Pankaj Kumar and Shamsher S. Bari

Volume 20, Issue 9, 2023

Published on: 17 May, 2023

Page: [883 - 891] Pages: 9

DOI: 10.2174/1570178620666230417084129

Price: $65

Abstract

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, 1H NMR, 13C NMR, and elemental analysis). Two different routes have been investigated for the substitution at the C-3 position of the azetidin-2-ones.

Keywords: Acetyl chloride, esterification, azetidin-2-one, microorganism, acetyl chloride, pharmacokinetics, FT-IR, monobactams.

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