Metal‐Free Cascade 1,4‐Conjugate Addition/Selective Annulation Strategy for Divergent Synthesis of Polysubstituted Imidazoles and 4‐Alkenylquinazolines

Advanced Synthesis & Catalysis, Год журнала: 2022, Номер 364(23), С. 4103 - 4109

Опубликована: Окт. 20, 2022

Abstract A metal‐free cascade annulation of propagylamines with amidines for divergent synthesis polysubstituted imidazoles and 4‐alkenylquinazolines has been developed. The reaction is believed to proceed by sequential 1,4‐conjugate addition propargylamines, 5‐ exo‐dig annulation/aromatization form the imidazoles, nucleophilic addition/elimination/aromatization quinazoline skeleton. In this reaction, a broad range electron‐rich, electron‐neutral, electron‐deficient react well give in 53–93% yields. Moreover, utility method was showcased gram‐scale experiments synthetic transformations product. magnified image

Язык: Английский

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Synthesis of arene-functionalized fused heterocyclic scaffolds via a regioselective cascade 1,4-conjugate addition/5-exo-dig annulation strategy

Organic & Biomolecular Chemistry, Год журнала: 2023, Номер 21(46), С. 9159 - 9172

Опубликована: Янв. 1, 2023

Facile access to furan fused heterocyclic scaffolds through a regioselective cascade reaction of propargylamines with 4-hydroxy-2H-pyran-2-ones and 4-hydroxy-6-methylpyridin-2(1H)-one has been achieved. This presumably involves the formation ortho-alkynyl quinone methide (o-AQM), 1,4-conjugate addition, followed by 5-exo-dig annulation, 1,3-H shift process. Moreover, provides new efficient method for synthesis highly sterically congested 3-phenolic furo[3,2-c]pyran-4-ones furo[3,2-c]pyridin-4(5H)-ones ring from readily available starting materials in good high yields (50-82%) broad functional group compatibility single step. Significantly, strategy described here is easily scalable several useful synthetic transformations prepared arene-functionalized 4H-furo[3,2-c]pyran-4-ones were also performed.

Язык: Английский

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Efficient synthesis of trisubstituted allenes via palladium-catalysed deaminative coupling of tertiary propargylamines with arylsiloxanes

Organic Chemistry Frontiers, Год журнала: 2024, Номер unknown

Опубликована: Ноя. 22, 2024

Highly regioselective and efficient synthesis of trisubstituted allenes with palladium catalysts via deaminative coupling reaction among tertiary propargylamines arylsiloxanes which were activated in situ using Et 3 N·3HF has been developed.

Язык: Английский

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Five-membered ring systems: with more than one N atom

Progress in heterocyclic chemistry, Год журнала: 2023, Номер unknown, С. 281 - 332

Опубликована: Янв. 1, 2023

Язык: Английский

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Six-membered ring systems: With O and/or S atoms

Progress in heterocyclic chemistry, Год журнала: 2023, Номер unknown, С. 493 - 568

Опубликована: Янв. 1, 2023

Язык: Английский

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