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

摘要

Starting from chlorosulfonyl isocyanate, successive addition of selected 1,2 and 1,3 haloalcohols, sulfamoylation with the nitrogen mustard and cyclization in alkaline conditions give title compounds in good yields. These sulfamoyloxazolidinones and sulfamoylperhydrooxazinones were revealed as efficient 2-chloroethylsulfamoyl donors in the 2-chloroethylnitrososulfamides synthesis; five new CENS (derivated from heterocyclic amines and amino acids) were thus synthezised. According to the experimental conditions, N-sulfamoylcyclocarbamates can be reopened by nucleophiles giving addition products by transcarbamoylation. Copyright (C) 1996 Elsevier Science Ltd [References: 22]