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Paper | Regular issue | Vol 83, No. 5, 2011, pp.1041-1056
Published online, 10th March, 2011
DOI: 10.3987/COM-11-12145
Synthesis, Crystal Structure and Antibacterial Evaluation of N-Substituted Perhydro-1,3-oxazin-2-ones Containing N-Phenylsulfonamide

Mounir Nessaib, Abdelghani Djahoudi, Achour Seridi, Hocine Akkari, Nour-Eddine Aouf, Jean-Claude Daran, and Mohamed Abdaoui*

*Laboratory of Applied Chemistry, University of May 8th, 1945, BP 401, Guelma, Algeria

Abstract

The synthesis of a new series of N-substituted perhydro-1,3-oxazin-2-ones containing N-phenylsulfonamide is described. The compounds 7a–7f were obtained in a one-pot reaction from chlorosulfonyl isocyanate, selected 1,3- halogenoalcohols and various aromatic amines in alkaline conditions, to give the target N-heterocyclic 6-membered ring compounds with good yields. The X-ray crystal structure of N-[(N-4-fluorophenyl)sulfamoyl]perhydro-1,3-oxazin-2-one 7d was solved. All the synthesized compounds have been screened for their in-vitro antibacterial activity against Staphylococcus aureus, Escherichia coli and Pseudomonas aeruginosa. Structures of 7d and 6e can be further optimized to give new potent antibacterial agents with structures significantly different from those of existing classes of antibiotics.