Synthesis of N-sulfamoyloxazolidinones and -perhydrooxazinones reactivity and use as donors in the Transsulfamoylation reaction; application to the preparation of 2-chloroethylnitrososulfamides. IV

Article abstract of DOI:10.1016/0040-4020(96)00860-5

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-chloroethylnitrosulfamides synthesis; five new CENS (derived 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.