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

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 pK(a) ~ 10 gave 4-dimethylamino-pyridinium arylsulfonyl-carbamoylides, while the more acidic heter...

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Detalles Bibliográficos
Autores principales: Sączewski, Franciszek, Kuchnio, Anna, Samsel, Monika, Łobocka, Marta, Kiedrowska, Agnieszka, Lisewska, Karolina, Sączewski, Jarosław, Gdaniec, Maria, Bednarski, Patrick J.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Molecular Diversity Preservation International 2010
Materias:
Article
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6257353/
https://www.ncbi.nlm.nih.gov/pubmed/20335967
http://dx.doi.org/10.3390/molecules15031113
Descripción
Sumario: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 pK(a) ~ 10 gave 4-dimethylamino-pyridinium arylsulfonyl-carbamoylides, while the more acidic heteroaryl sulfonamides (pK(a) ~ 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.

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