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Molecules 2010, 15(3), 1113-1126; doi:10.3390/molecules15031113
Article

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

1,* , 1, 1, 1, 1, 1, 1, 2 and 3
Received: 19 January 2010; in revised form: 26 February 2010 / Accepted: 26 February 2010 / Published: 26 February 2010
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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 4-dimethylaminopyridinium arylsulfonylcarbamoylides; 4-dimethylamino-pyridinium arylsulfonyl carbamates; arylsulfonyl ureas; heteroarylsulfonyl ureas; arylsulfonyl isocyanate substitutes
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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MDPI and ACS Style

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.

AMA Style

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.

Chicago/Turabian Style

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.


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