Visible-Light-Induced Intramolecular Radical Cyclization for the Synthesis of Benzimidazo-isoquinolineones and Pyrrolidones

A visible-light-induced radical cyclization of α-brominated amides has been developed to construct benzimidazole[2,1-<i>a</i>]isoquinolin-6(5<i>H</i>)-ones and pyrrolidonesin in yields up to 97%. The methodology exhibits a certain functional-group compatibility with 43 examples and operational simplicity, offering a rapid and concise approach to obtain five- and six-membered rings under the irradiation of 18 W blue LED. Additionally, large-scale reaction of this method for synthesizing benzimidazo-isoquinolineones and the further transformations to useful pyrrolidones were also conducted and afforded positive results.

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Publication Details

Journal
Organic Letters
Published
2024-12-12
DOI
https://doi.org/10.1021/acs.orglett.4c04292
Citations
7
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
1.75

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article

Visible-Light-Induced Intramolecular Radical Cyclization for the Synthesis of Benzimidazo-isoquinolineones and Pyrrolidones

Yangjie Wu, Kaixia Sui, Yuting Leng, Panpan Wang et al.
7 citations
Organic Letters
Radical Photochemical Reactions
1.75
article

Visible-Light-Induced Intramolecular Radical Cyclization for the Synthesis of Benzimidazo-isoquinolineones and Pyrrolidones

Yangjie Wu, Kaixia Sui, Yuting Leng, Panpan Wang, Ning Ma, Shiliang Jiang
article en
7 citations

Abstract

A visible-light-induced radical cyclization of α-brominated amides has been developed to construct benzimidazole[2,1-<i>a</i>]isoquinolin-6(5<i>H</i>)-ones and pyrrolidonesin in yields up to 97%. The methodology exhibits a certain functional-group compatibility with 43 examples and operational simplicity, offering a rapid and concise approach to obtain five- and six-membered rings under the irradiation of 18 W blue LED. Additionally, large-scale reaction of this method for synthesizing benzimidazo-isoquinolineones and the further transformations to useful pyrrolidones were also conducted and afforded positive results.

Organic LettersVol. 26(51)
Zhengzhou University (CN), State Key Laboratory of Oil and Gas Reservoir Geology and Exploitation (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 16%
Radical Photochemical Reactions
1.75
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Visible-Light-Induced Intramolecular Radical Cyclization for the Synthesis of Benzimidazo-isoquinolineones and Pyrrolidones — Yangjie Wu, Kaixia Sui, et al. · Organic Letters (2024) | TGRS Research Map | TGRS