Межі застосування частково ненасичених сультамів як дієнофілів і дієнів у реакції [4+2] циклоприєднання Дільса-Альдера
This study explores the reactivity of five- and six-membered sultams as both dienes and dienophiles in Diels-Alder reactions. As dienes in [4+2] cycloaddition, vinyl sultam bearing additional endocyclic C=C double bond reacted with highly electron-poor alkenes, i.e. maleimide, revealing that success...
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| Datum: | 2025 |
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| Hauptverfasser: | , , , , , |
| Format: | Artikel |
| Veröffentlicht: |
V.P. Kukhar Institute of Bioorganic Chemistry and Petrochemistry of the National Academy of Sciences of Ukraine
2025
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| Online Zugang: | https://bioorganica.com.ua/index.php/journal/article/view/93 |
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| Назва журналу: | Ukrainica Bioorganica Acta |
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Ukrainica Bioorganica Acta| Zusammenfassung: | This study explores the reactivity of five- and six-membered sultams as both dienes and dienophiles in Diels-Alder reactions. As dienes in [4+2] cycloaddition, vinyl sultam bearing additional endocyclic C=C double bond reacted with highly electron-poor alkenes, i.e. maleimide, revealing that successful cycloadduct formation occurred only under aqueous reflux conditions. Alternative conditions, including organic solvents and Lewis acid catalysis, failed to promote the reaction. Other dienophiles, such as acrylates and acetylene carboxylates, were ineffective, with sultam undergoing self-cycloaddition in moderate yields. As a dienophile, partially unsaturated sultam reacted selectively only with electron-enriched Danishefsky diene, forming fused sultam with an enone moiety. Other dienes, ranging from electron-enriched to electron-poor derivatives, did not react under the applied conditions, leaving the starting material unaltered. These results demonstrate the highly selective reactivity of sultams, influenced by their electronic properties, and provide valuable insights into their utility in synthetic organic chemistry |
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