Tandem chalcone-sulfonamide hybridization, cyclization and further Claisen–Schmidt condensation: Tuning molecular diversity through reaction time and order and catalyst
| Autor: | Andrea F. Moura, Felipe T. Martins, Manoel Odorico de Moraes, Aline Bernardes, Cameron Capeletti da Silva, Caridad N. Perez, Mirian R. C. de Castro, Raquel Ferreira Naves |
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| Jazyk: | angličtina |
| Rok vydání: | 2020 |
| Předmět: |
chemistry.chemical_classification
Chalcone Tandem General Chemical Engineering 02 engineering and technology General Chemistry 010402 general chemistry 021001 nanoscience & nanotechnology Ring (chemistry) 01 natural sciences Coupling reaction 0104 chemical sciences Catalysis Sulfonamide lcsh:Chemistry chemistry.chemical_compound chemistry lcsh:QD1-999 Nitro Organic chemistry Aldol condensation 0210 nano-technology |
| Zdroj: | Arabian Journal of Chemistry, Vol 13, Iss 1, Pp 1345-1354 (2020) |
| ISSN: | 1878-5352 |
| Popis: | We here report the synthesis of novel chalcone-sulfonamide compounds based on the hybridization at 2′ position and nitro substitution at the side chalcone phenyl ring followed by tandem cyclization into quinolinone derivatives and then a further aldol condensation only as a function of the reaction time. Therefore, for the first time, we have controlled the sequential preparation of chalcone-sulfonamide hybrids, quinolinones and then (E)-3-ene-2,3-dihydroquinolinones simply stopping reaction over increasing time periods. Furthermore, a new molecular scaffold based on a chalcone-(bis)sulfonamide hybrid has been gotten through changing the sequence of coupling reactions and catalyst. This study means practical and useful ways of constructing in high yields new biologically active compounds bearing diversified molecular scaffolds. Keywords: Molecular hybridization, Chalcone, Sulfonamide, Quinolinone, Tandem reactions, Claisen–Schmidt condensation |
| Databáze: | OpenAIRE |
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