Synthesis of fused-pyran derivatives <i>via</i> a base-mediated annulation of bis-allenoates followed by auto-oxidation in air

Zhao, Jun-Bo; Yang, Jing-Kui

doi:10.1039/d4ob00835a

Org. Biomol. Chem.

2024

DOI: 10.1039/d4ob00835a

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Synthesis of fused-pyran derivatives via a base-mediated annulation of bis-allenoates followed by auto-oxidation in air

Jun-Bo Zhao,

Jing-Kui Yang

Abstract: We introduce, for the first time, an inorganic base-mediated cyclization and auto-oxidation of bisallenones/bisalkynones. This reaction is realized under mild conditions through precise control of the base and atmosphere, providing...

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2024

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

Rajapaksa,

Yan Wong,

Lee

2024

Chemistry A European J

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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.

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

Rajapaksa,

Yan Wong,

Lee

2024

Chemistry A European J

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show abstract

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Synthesis of fused-pyran derivatives via a base-mediated annulation of bis-allenoates followed by auto-oxidation in air

Abstract: We introduce, for the first time, an inorganic base-mediated cyclization and auto-oxidation of bisallenones/bisalkynones. This reaction is realized under mild conditions through precise control of the base and atmosphere, providing...

Cited by 1 publication

References 33 publications

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

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

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