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Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest
Department of Chemical Technology of Drugs, Faculty of Pharmacy, Medical University of Gdańsk, 80-416 Gdańsk, Poland
Faculty of Chemistry, A. Mickiewicz University, 60-780 Poznań, Poland
Department of Pharmaceutical and Medicinal Chemistry, Institute of Pharmacy, University of Greifswald, D-17487 Greifswald, Germany
* Author to whom correspondence should be addressed.
Received: 19 January 2010; in revised form: 26 February 2010 / Accepted: 26 February 2010 / Published: 26 February 2010
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
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Sączewski, F.; Kuchnio, A.; Samsel, M.; Łobocka, M.; Kiedrowska, A.; Lisewska, K.; Sączewski, J.; Gdaniec, M.; Bednarski, P.J. Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest. Molecules 2010, 15, 1113-1126.
Sączewski F, Kuchnio A, Samsel M, Łobocka M, Kiedrowska A, Lisewska K, Sączewski J, Gdaniec M, Bednarski PJ. Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest. Molecules. 2010; 15(3):1113-1126.
Sączewski, Franciszek; Kuchnio, Anna; Samsel, Monika; Łobocka, Marta; Kiedrowska, Agnieszka; Lisewska, Karolina; Sączewski, Jarosław; Gdaniec, Maria; Bednarski, Patrick J. 2010. "Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest." Molecules 15, no. 3: 1113-1126.