SYNTHESIS OF N-SULFAMOYLOXAZOLIDINONES AND N-PERHYDROOXAZINONES REACTIVITY AND USE AS DONORS IN THE TRANSSULFAMOYLATION REACTION - APPLICATION TO THE PREPARATION OF 2-CHLORETHYLNITROSOSULFAMIDES .4.

Authors
DEWYNTER G ABDAOUI M REGAINIA Z MONTERO JL
Citation
G. Dewynter et al., SYNTHESIS OF N-SULFAMOYLOXAZOLIDINONES AND N-PERHYDROOXAZINONES REACTIVITY AND USE AS DONORS IN THE TRANSSULFAMOYLATION REACTION - APPLICATION TO THE PREPARATION OF 2-CHLORETHYLNITROSOSULFAMIDES .4., Tetrahedron, 52(45), 1996, pp. 14217-14224
Citations number
22
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
52
Issue
45
Year of publication
1996
Pages
14217 - 14224
Database
ISI
SICI code
0040-4020(1996)52:45<14217:SONANR>2.0.ZU;2-P
Abstract
Starting from chlorosulfonyl isocyanate, successive addition of select ed 1,2 and 1,3 haloalcohols, sulfamoylation with the nitrogen mustard and cyclization in alkaline conditions give title compounds in good yi elds. These sulfamoyloxazolidinones and sulfamoylperhydrooxazinones we re revealed as efficient 2-chloroethylsulfamoyl donors in the 2-chloro ethylnitrososulfamides synthesis; five new CENS (derivated from hetero cyclic amines and amino acids) were thus synthezised. According to the experimental conditions, N-sulfamoylcyclocarbamates can be reopened b y nucleophiles giving addition products by transcarbamoylation. Copyri ght (C) 1996 Elsevier Science Ltd