Tetrahedron letters

Expedient synthesis of 2-chloroethylnitrososulfamides (CENS) via the decarboxylative reopening of sulfamoyloxazolidinones

M Abdaoui, G Dewynter, JL Montero

Index: Abdaoui, Mohamed; Dewynter, Georges; Montero, Jean-Louis Tetrahedron Letters, 1996 , vol. 37, # 32 p. 5695 - 5698

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Citation Number: 30

Abstract

The synthesis of chloroethylnitrososulfamide,(CENS), was carried out starting from chlorosulfonyl isocyanate, amines and haloalcohols through heterocyclization and decarboxylative reopening of N-sulfamoyl-2-oxazolidinones. A total regioselectivity concerning CO2 versus SO2 site hydrolysis was observed. A related aminolysis of sulfamoyloxazolidinones gave N-carbamoylsulfamides. The specific nitrosation on the N- ...