S. Beaudoin, K. E. Kinsey, J. F. Burns
Jan 10, 2003
Citations
0
Influential Citations
41
Citations
Journal
The Journal of organic chemistry
Abstract
The synthetic methods reported in the literature for the preparation of sulfonylureas tend to be restricted in scope or unsuitable for use in parallel synthesis. We have developed a method for preparing sterically congested sulfonylureas based on N,N'-sulfuryldiimidazole that is both convenient and amenable to parallel synthesis. Sequential activation by way of alkylation of the imidazole group using methyl triflate followed by nucleophilic displacement with a variety of amines and anilines afford the unsymmetrical sulfonylurea. Sulfonylureas prepared from anilines were obtained in high yields using N,N'-sulfuryldiimidazole, while the somewhat more sterically congested analogue, N,N'-sulfurylbis-2-methylimidazole, proved to be superior for alkylamines.