Design and synthesis of fused cyclic sulfamides-oxazolidinones. Issue 10 (8th March 2019)

• Record Type: Journal Article
• Authors: Rmedi, Hamdi
• Is Part Of: Tetrahedron. Volume 75:Issue 10(2019)
• Page Start: 1337
• Page End: 1342
• Publication Date: 2019-03-08
• Subjects: Oxazolidinone -- Cyclic sulfamide -- 2, 3-Dibromopropanol -- Chlorosulfonylisocyanate -- N-carboxylsulfamide -- N-sulfamoyloxazolidinone; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tet.2019.01.046
• Languages: English
• ISSNs: 0040-4020

Abstract

Abstract: An efficient protocol for the synthesis of a new series of oxazolidin-2-ones containing sulfamide moieties is described. The synthesis was achieved in two reaction steps. The first was carried out under anhydrous conditions at 0 °C through a selective addition of an alcohol and primary amines to chlorosulfonylisocyanate to produce N -carboxylsulfamides in good yields. Under appropriate conditions of solvent, base and temperature, these intermediates underwent subsequent intramolecular cyclizations, giving exclusively the corresponding sulfamoyloxazolidinones. Graphical abstract: Image 1