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Facile Synthesis of Novel C-3 Monosubstituted 3-phenylthio-β-lactams

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Author Affiliations

  • 1Department of Chemistry and Centre of Advanced Studies in Chemistry, Panjab University, Chandigarh-160014, INDIA

Res.J.chem.sci., Volume 3, Issue (7), Pages 45-53, July,18 (2013)

Abstract

An efficient and operationally simple strategy for the synthesis of C-3 monosubstituted monocyclic β-lactams is described. Treatment of ethyl 2-phenylthioethanoate (1) with SO2Cl2 in dry methylene chloride at 0°C yields ethyl 2-chloro-2-phenylthioethanoate(2). Lewis acid (TiCl4, SnCl4 and ZnCl2) mediated functionalization of (2) using various aliphatic and aromatic compounds (nucleophiles) gives monosubstituted phenythioethanoates (3a-e). These esters on basic hydrolysis and subsequent acidification gave monosubstituted phenythioethanoic acids (4a-e). Reaction of these phenythioethanoic acids and appropriate imines in the Staudinger reaction using POCl3 as condensing agent led to the synthesis of novel C-3 monosubstituted 3-phenylthio-β-lactams.

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