Radical Cascade Cyclization of Alkene‐Tethered Compounds: Versatile Approach towards Ring‐Fused Polycyclic Structures

Asian Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 12(5)

Published: April 8, 2023

Abstract Ring‐fused polycyclic structures widely exist in a myriad of natural products and pharmaceutical molecules. Consequently, the construction such from readily available substrates becomes an important researching topic organic synthesis. Triggered by addition radicals to (activated or unactivated) double bonds alkenes, subsequent intramolecular addition/cyclization leads compounds. Following this procedure, variety functionalized ring‐fused were formed. Great achievements have been witnessed recently. Those works provided efficient, atom economy, operational simple approaches toward versatile alkene‐based substrates. Here, we summarized recent on formation via radical‐triggered cascade reactions alkenes. Construction with no less than 3 fused rings developed during last decade included Review, corresponding mechanisms also discussed.

Language: Английский

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Visible‐Light‐Driven Cyclizations

Advanced Synthesis & Catalysis, Journal Year: 2024, Volume and Issue: 366(4), P. 635 - 697

Published: Jan. 13, 2024

Abstract In recent years, the interest to develop cyclizations promoted by visible light has been gaining a lot of attention due its sustainability aspect. this review, we summarize most important advances in period describing methods used generate different ring sizes, while focusing on mechanistic details these reactions.

Language: Английский

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Visible Light-Induced Radical Cascade Difluoromethylation/Cyclization of Unactivated Alkenes: Access to CF₂H-Substituted Polycyclic Imidazoles

ACS Omega, Journal Year: 2024, Volume and Issue: 9(26), P. 28129 - 28143

Published: June 19, 2024

An efficient and mild protocol for the visible light-induced radical cascade difluoromethylation/cyclization of imidazoles with unactivated alkenes using easily accessible bench-stable difluoromethyltriphenylphosphonium bromide as precursor -CF

Language: Английский

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Recent advances in the synthesis of benzimidazolo[2,1-a]isoquinoline-6(5H)-one derivatives from N-methylacryloyl-2-arylbenzimidazoles

Tetrahedron, Journal Year: 2024, Volume and Issue: 160, P. 134050 - 134050

Published: May 25, 2024

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 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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Divergent Construction of Azaheterocycles via Alkoxyl Radical-Triggered C–C Bond Cleavage/Cyclization of N-Functionalized Acrylamides

The Journal of Organic Chemistry, Journal Year: 2023, Volume and Issue: 88(14), P. 9927 - 9940

Published: July 11, 2023

An array of redox-neutral alkylation/cyclization cascade reactions N-functionalized acrylamides with cycloalkyl hydroperoxides were achieved via the alkoxyl radical-triggered C-C bond cleavage. Through adjusting radical acceptors on N atom, a variety keto-alkylated chain-containing azaheterocycles, including indolo[2,1-a]isoquinolin-6(5H)-ones, quinoline-2,4-diones, and pyrido[4,3,2-gh]phenanthridines constructed by one-pot procedure good yields excellent functional group tolerance.

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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Synthesis of Acylation Polycyclic Derivatives via Regioselective Acylation/Cyclization of 1,7-Dienes with Acyl Oxime Esters

The Journal of Organic Chemistry, Journal Year: 2024, Volume and Issue: 89(16), P. 11233 - 11243

Published: July 25, 2024

A visible-light-induced radical cascade regioselective acylation/cyclization of 1,7-dienes with acyl oxime esters for the preparation acylation polycyclic compounds via NCR-mediated C-C σ-bond cleavage is established. The transformation involves in and selective addition electron neutral C═C bonds synthesis quinolinone derivatives, not traditional seven-membered ring products. strategy offers several advantages, including broad substrate tolerance, no need bases, hyperstoichiometric initiators, other auxiliaries.

Language: Английский

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