Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest

Abstract

The course of reaction of aryl and heteroaryl sulfonamides with diphenylcarbonate (DPC) and 4-dimethylaminopyridine (DMAP) was found to depend on the pKa of the sulfonamide used. Aryl sulfonamides with pKa ~ 10 gave 4-dimethylamino-pyridinium arylsulfonyl-carbamoylides, while the more acidic heteroaryl sulfonamides (pKa ~ 8) furnished 4-dimethylaminopyridinium heteroarylsulfonyl carbamates. Both the carbamoylides and carbamate salts reacted with aliphatic and aromatic amines with the formation of appropriate aryl(heteroaryl)sulfonyl ureas, and therefore, can be regarded as safe and stable substitutes of the hazardous and difficult to handle aryl(heteroaryl)sulfonyl isocyanates.

Keywords

• 4-dimethylaminopyridinium arylsulfonylcarbamoylides
• 4-dimethylamino-pyridinium arylsulfonyl carbamates
• arylsulfonyl ureas
• heteroarylsulfonyl ureas
• arylsulfonyl isocyanate substitutes