Design and synthesis of fused cyclic sulfamides-oxazolidinones

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.