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 pKa ~ 10 gave 4-dimethylamino-pyridinium arylsulfonyl-carbamoylides, while the more acidic heteroa...
| Main Authors: | , , , , , , , , |
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| Format: | Article |
| Language: | English |
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MDPI AG
2010-02-01
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| Series: | Molecules |
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| Online Access: | http://www.mdpi.com/1420-3049/15/3/1113/ |
| _version_ | 1818144095420284928 |
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| author | Maria Gdaniec Jarosław Sączewski Karolina Lisewska Agnieszka Kiedrowska Marta Łobocka Monika Samsel Anna Kuchnio Franciszek Sączewski Patrick J. Bednarski |
| author_facet | Maria Gdaniec Jarosław Sączewski Karolina Lisewska Agnieszka Kiedrowska Marta Łobocka Monika Samsel Anna Kuchnio Franciszek Sączewski Patrick J. Bednarski |
| author_sort | Maria Gdaniec |
| collection | DOAJ |
| description | 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. |
| first_indexed | 2024-12-11T11:42:07Z |
| format | Article |
| id | doaj.art-16dec54163c5414d86f5ac752794aa7b |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-12-11T11:42:07Z |
| publishDate | 2010-02-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-16dec54163c5414d86f5ac752794aa7b2022-12-22T01:08:35ZengMDPI AGMolecules1420-30492010-02-011531113112610.3390/molecules15031113Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological InterestMaria GdaniecJarosław SączewskiKarolina LisewskaAgnieszka KiedrowskaMarta ŁobockaMonika SamselAnna KuchnioFranciszek SączewskiPatrick J. BednarskiThe 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.http://www.mdpi.com/1420-3049/15/3/1113/4-dimethylaminopyridinium arylsulfonylcarbamoylides4-dimethylamino-pyridinium arylsulfonyl carbamatesarylsulfonyl ureasheteroarylsulfonyl ureasarylsulfonyl isocyanate substitutes |
| spellingShingle | Maria Gdaniec Jarosław Sączewski Karolina Lisewska Agnieszka Kiedrowska Marta Łobocka Monika Samsel Anna Kuchnio Franciszek Sączewski Patrick J. Bednarski Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest Molecules 4-dimethylaminopyridinium arylsulfonylcarbamoylides 4-dimethylamino-pyridinium arylsulfonyl carbamates arylsulfonyl ureas heteroarylsulfonyl ureas arylsulfonyl isocyanate substitutes |
| title | Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest |
| title_full | Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest |
| title_fullStr | Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest |
| title_full_unstemmed | Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest |
| title_short | Synthesis of Novel Aryl(heteroaryl)sulfonyl Ureas of Possible Biological Interest |
| title_sort | synthesis of novel aryl heteroaryl sulfonyl ureas of possible biological interest |
| topic | 4-dimethylaminopyridinium arylsulfonylcarbamoylides 4-dimethylamino-pyridinium arylsulfonyl carbamates arylsulfonyl ureas heteroarylsulfonyl ureas arylsulfonyl isocyanate substitutes |
| url | http://www.mdpi.com/1420-3049/15/3/1113/ |
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