Cascade Reactions of Alkynyl Ketones and Amides to Generate Unsaturated Oxacycles and Aromatic Carbocycles

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Abstract: We describe novel amine‐mediated transformation of alkynyl ketones and amides to generate 2‐methylene‐2H‐pyrans, substituted 3‐hydroxy‐9H‐fluoren‐9‐ones, and amine‐incorporated arenes. These cascade processes are initiated by conjugate addition of secondary amine followed by hydrolysis of the enamine/vinylogous amide intermediates. The product distribution is highly sensitive to the steric and electronic effects of the substituents on both the alkyne moieties, the tether structure connecting them, and the nature of the amine. Alkynyl amide participates in the Alder‐ene reaction favorably to generate more reactive allene amide that reacts with amine to generate amine‐incorporated arene products. These metal‐free cascade reactions are a useful synthetic method that can be exploited for the construction of various hetero‐ and carbocyclic systems.

Location: Deutsche Nationalbibliothek Frankfurt am Main

Extent: Online-Ressource

Language: Englisch

Bibliographic citation: Cascade Reactions of Alkynyl Ketones and Amides to Generate Unsaturated Oxacycles and Aromatic Carbocycles ; day:05 ; month:11 ; year:2024 ; extent:7
Chemistry - a European journal ; (05.11.2024) (gesamt 7)

Creator: Rajapaksa, Kumudi J. W.
Yan Wong, Hang
Lee, Daesung

DOI: 10.1002/chem.202403270

URN: urn:nbn:de:101:1-2411051337546.823166666997

Rights: Open Access; Der Zugriff auf das Objekt ist unbeschränkt möglich.

Last update: 15.08.2025, 7:35 AM CEST

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Rajapaksa, Kumudi J. W.
Yan Wong, Hang
Lee, Daesung

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Cascade Reactions of Alkynyl Ketones and Amides to Generate Unsaturated Oxacycles and Aromatic Carbocycles

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