4.7 Article

N-Sulfenylation of β-Lactams: Radical Reaction of N-Bromo-azetidinones by TEMPO Catalysis

Journal

JOURNAL OF ORGANIC CHEMISTRY
Volume 88, Issue 20, Pages 14728-14735

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.3c01759

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This study reports a versatile synthesis strategy for N-sulfenylated azetidinones using TEMPO radical as the catalyst and disulfides. The reaction conditions were optimized to achieve high yields of N-alkylthio- or N-arylthio-azetidinones, demonstrating a good substrate scope.
Azetidinones with a sulfenyl group on the beta-lactam nitrogen atom show interesting biological activities as antimicrobial agents and enzyme inhibitors. We report in the present study a versatile synthesis of N-sulfenylated azetidinones starting from the corresponding N-bromo derivatives by means of the (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) radical as the catalyst and disulfides. Preparation of N-halo-azetidinones was studied and optimized. The reactivity of N-bromo-azetidinone 2a as a model compound in the presence of TEMPO radical was investigated by NMR and electron paramagnetic resonance (EPR) spectroscopy studies. Optimization of the reaction conditions allowed the access of N-alkylthio- or N-arylthio-azetidinones from 55 to 92% yields, and the method exhibited a good substrate scope.

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