Photocatalytic synthesis of carbamoylated chroman-4-ones via radical cascade cyclization of 2-(allyloxy)arylaldehydes and oxamic acids

Molecular Catalysis, Journal Year: 2025, Volume and Issue: 582, P. 115168 - 115168

Published: May 2, 2025

Language: Английский

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Propargyl Chalcones’ Radical Annulation/Sulfonation Reaction: Efficient Synthesis of Benzo[b]oxepin-5(2H)-one and Chromane Derivatives

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(11), P. 7136 - 7149

Published: May 24, 2022

A novel and facile methodology for the synthesis of sulfonated benzo[b]oxepinone chromane derivatives was reported by reaction propargyl chalcones with arylsulfonyl chloride via radical cascade annulation/sulfonation under laboratory conditions. Readily available chalcones, commercialized chloride, simple conditions make this six(seven)-membered oxygen-containing heterocycles' synthetic strategy more attractive significant application values.

Language: Английский

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Visible-light-induced acylation/cyclization of active alkenes: facile access to acylated isoquinolinones

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(18), P. 3767 - 3778

Published: Jan. 1, 2022

Nitrogen heterocycles, especially polycyclic compounds, are significant skeletons in valuable molecules. Herein, we developed an efficient and practical visible-light-induced acylation/cyclization of active alkenes with acyl oxime derivatives for constructing acylated indolo/benzimidazo-[2,1,a]isoquinolin-6(5H) ones. This reaction was compatible various functional groups a series fused indole/imidazole were prepared up to 95% yield at room temperature.

Language: Английский

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Recent Advances in Molecule Synthesis Involving C-C Bond Cleavage of Ketoxime Esters

Molecules, Journal Year: 2023, Volume and Issue: 28(6), P. 2667 - 2667

Published: March 15, 2023

The synthetic strategies of oxime derivatives participating in radical-type reactions have been rapidly developed the last few decades. Among them, N–O bond cleavage esters leading to formation nitrogen-centered radicals triggers adjacent C–C produce carbon-centered free radicals, which has virtually used organic synthesis recent years. Herein, we summarized radical involving and through this special reaction form, including those from acyl ester cyclic ketoxime derivatives. These contents were systematically classified according different types. In review, after 2021 included, with emphasis on substrate scope mechanism.

Language: Английский

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Visible light-induced radical cascade acylmethylation/cyclization of 2-(allyloxy)arylaldehydes with α-bromo ketones: access to cyclic 1,5-dicarbonyl-containing chroman-4-one skeletons

Organic & Biomolecular Chemistry, Journal Year: 2023, Volume and Issue: 21(33), P. 6772 - 6777

Published: Jan. 1, 2023

A novel photocatalytic protocol for effective and efficient synthesis of cyclic 1,5-diketones containing chroman-4-one skeletons in moderate to good yields via radical cascade acylmethylation/cyclization 2-(allyloxy)arylaldehydes with α-bromo ketones has been described. This reaction features a broad substrate scope, functional group tolerance, metal- oxidant-free conditions. An acylmethyl radical-triggered cyclization was involved.

Language: Английский

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Visible-Light-Induced Cascade Cyclization of N-Propargyl Aromatic Amines and Acyl Oxime Esters: Rapid Access to 3-Acylated Quinolines

The Journal of Organic Chemistry, Journal Year: 2022, Volume and Issue: 87(15), P. 10277 - 10284

Published: July 6, 2022

Visible-light-induced radical cascade acylation/cyclization/aromatization of N-propargyl aromatic amines and acyl oxime esters for the construction 3-acylated quinolines is developed. This approach uses as precursor radicals well acylation reagents, Eosin Y photocatalyst, acetonitrile solvent, providing a convenient route toward via C-C bond cleavage esters.

Language: Английский

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Metal- and photocatalyst-free approach to visible-light-induced acylation of quinoxalinones

Organic & Biomolecular Chemistry, Journal Year: 2024, Volume and Issue: 22(29), P. 5924 - 5929

Published: Jan. 1, 2024

A transition-metal- and photocatalyst-free photochemical acylation strategy driven by the photoexcitation of an electron donor–acceptor (EDA) complex has been developed.

Language: Английский

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Recent advances in free radical cyclizations of 2-alkenyl benzaldehydes to synthesize benzocycloketones

New Journal of Chemistry, Journal Year: 2022, Volume and Issue: 46(44), P. 21013 - 21026

Published: Jan. 1, 2022

Radical reactions involving 2-alkenyl benzaldehydes have intensively progressed and give unique access to structurally valuable benzocycloketone compounds.

Language: Английский

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Cu-catalyzed oxidative denitrogenation of 3-aminoindazoles for the synthesis of isoquinolinones

Organic & Biomolecular Chemistry, Journal Year: 2022, Volume and Issue: 20(34), P. 6844 - 6853

Published: Jan. 1, 2022

A Cu-catalyzed oxidative dual arylation of active alkenes via the cleavage two C-N bonds 3-aminoindazoles is presented for constructing isoquinolinones. Importantly, are used as efficient arylating agents through a radical process. This method has good substrate scope and functional group compatibility.

Language: Английский

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Photoredox-catalyzed intramolecular oxy- and aminoacylation of alkenes with acyl oxime esters: facile synthesis of acylated saturated heterocycles

Organic Chemistry Frontiers, Journal Year: 2023, Volume and Issue: 11(1), P. 74 - 82

Published: Nov. 17, 2023

In the present paper, an efficient photoredox-catalyzed intramolecular oxy- and aminoacylation of internal alkenes equipped with pendant oxygen- or nitrogen-centered nucleophiles acyl oxime esters is reported. Under visible-light irradiation, a variety structurally diverse acylated saturated heterocycles, such as tetrahydrofurans, tetrahydropyrans, δ-valerolactones, tetrahydropyrroles, piperidines, tetrahydro-1,3-oxazepines, etc., were efficiently synthesized from easily accessible unsaturated alcohols, carboxylic acids, tosyl-protected amines, O-homoallyl benzimidates via radical-mediated cascade acylation/cyclization process. This light-driven transformation features broad substrate scope, good functional group compatibility, high regio- diastereoselectivity, mild reaction conditions, representing general practical procedure toward construction heterocycles well their derivatives.

Language: Английский

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