EXPEDIENT SYNTHESIS OF 2-CHLOROETHYLNITROSOSULFAMIDES (CENS) VIA THE DECARBOXYLATIVE REOPENING OF SULFAMOYLOXAZOLIDINONES

Authors
ABDAOUI M DEWYNTER G MONTERO JL
Citation
M. Abdaoui et al., EXPEDIENT SYNTHESIS OF 2-CHLOROETHYLNITROSOSULFAMIDES (CENS) VIA THE DECARBOXYLATIVE REOPENING OF SULFAMOYLOXAZOLIDINONES, Tetrahedron letters, 37(32), 1996, pp. 5695-5698
Citations number
29
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
37
Issue
32
Year of publication
1996
Pages
5695 - 5698
Database
ISI
SICI code
0040-4039(1996)37:32<5695:ESO2(V>2.0.ZU;2-9
Abstract
The synthesis of chloroethylnitrososulfamides (CENS), was carried out starting from chlorosulfonyl isocyanate, amines and haloalcohols throu gh heterocyclization and decarboxylative reopening of N-sulfamoyl-2-ox azolidinones. A total regioselectivity concerning CO2 versus SO2 site hydrolysis was observed. A related aminolysis of sulfamoyloxazolidinon es gave N-carbamoylsulfamides. The specific nitrosation on the N-chlor oalkyl moiety can be obtained after methylation of the sulfamoyloxazol idinones. Copyright (C) 1996 Elsevier Science Ltd