Photoredox radical cyclization reaction of <i>o</i>-vinylaryl isocyanides with acyl chlorides to access 2,4-disubstituted quinolines

Huang, Peng-Fei; Fu, Jia-Le; Huang, Jia-Jing; Xiong, Bi-Quan; Tang, Ke-Wen; Liu, Yu

doi:10.1039/d3ob01915b

Org. Biomol. Chem.

2024

DOI: 10.1039/d3ob01915b

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Photoredox radical cyclization reaction of o-vinylaryl isocyanides with acyl chlorides to access 2,4-disubstituted quinolines

Peng-Fei Huang,

Jia-Le Fu,

Jia-Jing Huang

et al.

Abstract: A photoredox radical cascade cyclization reaction for the effective construction of 2,4-disubstituted quinolines at room temperature is described. It shows good substrate suitability and functional group compatibility.

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Cited by 3 publications

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A New Method of Constructing Methyleneindene and Quinoline Frameworks from Methylenecyclopropanes

Yang,

Shi,

Wei

2024

Chemistry An Asian Journal

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In this paper, we have established an operationally convenient protocol for the rapid construction of polysubstituted methyleneindene and quinoline derivatives under mild conditions. This new synthetic method is achieved through the conversion of acetyl‐substituted methylenecyclopropanes with TsOH·H2O and ortho‐amino‐substituted methylenecyclopropanes with aromatic aldehyde and TsOH·H2O, respectively. A variety of transformations of the obtained products was demonstrated. The plausible reaction mechanisms were also proposed.

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A New Method of Constructing Methyleneindene and Quinoline Frameworks from Methylenecyclopropanes

Yang,

Shi,

Wei

2024

Chemistry An Asian Journal

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FeF₃‐Promoted Radical Fluoroalkylation of o‐Alkenylaryl Isocyanides to Access 2‐Fluoroalkylated Quinolines

Zhou,

Zhang,

et al. 2024

Eur J Org Chem

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Photoredox-Catalyzed C-Indolyl/Quinolyl Glycosylation from 2-Styrylisocyanides and Glycosyl Bromides

Jiao,

Shi,

Yang

et al. 2024

Org. Lett.

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Indole and quinoline structures are present in numerous biologically active molecules, making the synthesis of their glycosylation products a subject of extensive research and interest in drug development. Here, we report a photoredox strategy for the synthesis of C-indolyl and C-quinolyl glycosides using 2styrylisocyanides and glycosyl bromides as building blocks. This approach offers mild reaction conditions, high α-selectivity, and scalability for large-scale reactions. The radical cyclization mode switching from 5-exo-trig to 6-endo-trig is achieved by selecting the substituents on the 2-vinyl group. This strategy enriches the toolbox of heterocyclic glycosylation methods and benefits advances in research on heteroaryl-based pharmaceuticals.

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Photoredox radical cyclization reaction of o-vinylaryl isocyanides with acyl chlorides to access 2,4-disubstituted quinolines

Abstract: A photoredox radical cascade cyclization reaction for the effective construction of 2,4-disubstituted quinolines at room temperature is described. It shows good substrate suitability and functional group compatibility.

Cited by 3 publications

References 99 publications

A New Method of Constructing Methyleneindene and Quinoline Frameworks from Methylenecyclopropanes

A New Method of Constructing Methyleneindene and Quinoline Frameworks from Methylenecyclopropanes

FeF₃‐Promoted Radical Fluoroalkylation of o‐Alkenylaryl Isocyanides to Access 2‐Fluoroalkylated Quinolines

Photoredox-Catalyzed C-Indolyl/Quinolyl Glycosylation from 2-Styrylisocyanides and Glycosyl Bromides

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About

Photoredox radical cyclization reaction of o-vinylaryl isocyanides with acyl chlorides to access 2,4-disubstituted quinolines

Abstract: A photoredox radical cascade cyclization reaction for the effective construction of 2,4-disubstituted quinolines at room temperature is described. It shows good substrate suitability and functional group compatibility.

Cited by 3 publications

References 99 publications

A New Method of Constructing Methyleneindene and Quinoline Frameworks from Methylenecyclopropanes

A New Method of Constructing Methyleneindene and Quinoline Frameworks from Methylenecyclopropanes

FeF3‐Promoted Radical Fluoroalkylation of o‐Alkenylaryl Isocyanides to Access 2‐Fluoroalkylated Quinolines

Photoredox-Catalyzed C-Indolyl/Quinolyl Glycosylation from 2-Styrylisocyanides and Glycosyl Bromides

Contact Info

Product

Resources

About

FeF₃‐Promoted Radical Fluoroalkylation of o‐Alkenylaryl Isocyanides to Access 2‐Fluoroalkylated Quinolines