Parallel Liquid-Phase Synthesis of N-Substituted 6-Aminosulfonyl-2-oxo-1,2-dihydroquinoline-4-carboxamide and 6-Aminosulfonylquinoline-4-carboxamide Derivatives
| Autor: | Alexey P. Ilyn, Caroline Williams, Dmitry V. Kravchenko, Julia A. Kuzovkova, Alexander Viktorovich Khvat, Vladimir V. Kobak, Alexandre V. Ivachtchenko, Volodymir M. Kysil |
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| Rok vydání: | 2005 |
| Předmět: |
chemistry.chemical_classification
Sulfonamides Molecular Structure Chemistry medicine.drug_class Isatin Quinoline Carboxamide General Chemistry General Medicine Pfitzinger reaction Combinatorial chemistry Diethyl malonate Sulfonamide chemistry.chemical_compound Drug Design Reagent Quinolines medicine Combinatorial Chemistry Techniques 6-aminosulfonylquinoline-4-carboxamide |
| Zdroj: | ChemInform. 36 |
| ISSN: | 1522-2667 0931-7597 |
| DOI: | 10.1002/chin.200532145 |
| Popis: | Two efficient strategies for solution-phase parallel synthesis of libraries of quinoline derivatives are described. The first synthetic pathway features the Pfitzinger reaction of isatin with diethyl malonate and sulfochlorination of the resulting 2-oxo-1,2-dihydroquinoline-4-carboxylate followed by generation of sulfonamide library. The second strategy employs the unusual behavior of 5-sulfamoylisatins in Pfitzinger reactions, which results in formation of 6-sulfamoyl-4-carboxyquinolines instead of the anticipated 2-oxo-1,2-dihydroquinoline structures. The obtained carboxylates appeared to be convenient synthetic intermediates for the generation of the corresponding carboxamide libraries. Using these reagents, the parallel solution-phase synthesis of more than 500 substituted quinoline and 2-oxo-1,2-dihydroquinoline derivatives has been accomplished on the 50-100-mg scale. Simple manual techniques for parallel reactions using special CombiSyn synthesizers were coupled with easy purification procedures to give high-purity final products. The scope and limitations of the developed approaches are discussed. |
| Databáze: | OpenAIRE |
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