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Synthesis and Elimination Pathways of 1-Methanesulfonyl-1,2-dihydroquinoline Sulfonamides
A series of new Morita–Baylis–Hillman acetates were prepared and reacted with methanesulfonamide (K(2)CO(3), DMF, 23 °C) to produce tertiary dihydroquinoline sulfonamides in high yields. Subsequent efforts to eliminate the methylsulfonyl group from these derivatives (K(2)CO(3), DMF, 90 °C) as a rout...
Autores principales: | , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2023
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Materias: | |
Acceso en línea: | https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10096818/ https://www.ncbi.nlm.nih.gov/pubmed/37050020 http://dx.doi.org/10.3390/molecules28073256 |
Sumario: | A series of new Morita–Baylis–Hillman acetates were prepared and reacted with methanesulfonamide (K(2)CO(3), DMF, 23 °C) to produce tertiary dihydroquinoline sulfonamides in high yields. Subsequent efforts to eliminate the methylsulfonyl group from these derivatives (K(2)CO(3), DMF, 90 °C) as a route to quinolines were met with mixed results. Although dihydroquinoline sulfonamides prepared from ethyl acrylate and acrylonitrile generally underwent elimination to give excellent yields of quinolines, those generated from 3-buten-2-one failed to undergo elimination and instead decomposed. The failure of these ketone substrates to aromatize presumably derives from the enolizable methyl ketone at C-3. Finally, the attempted aromatization of the acrylate-derived 6,7-difluoro-1,2-dihydroquinoline sulfonamide demonstrated that other interesting processes could occur in preference to the desired elimination. |
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