Issue 21, 2024
From the journal:

Chemical Communications

Visible-light-driven EDA complex-promoted cascade cyclization to construct 4-cyanoalkyl isoquinoline-1,3-diones†

Dong-Liang Zhang,a   Zhang-Gao Le,*a   Qing Li,a   Zong-Bo Xie, ORCID logo a   Wen-Wen Yanga  and  Zhi-Qiang Zhu ORCID logo *a  

* Corresponding authors

a Jiangxi Province Key Laboratory of Synthetic Chemistry, School of Chemistry and Material Science, East China University of Technology, Nanchang, Jiangxi, China
E-mail: zhuzq@ecut.edu.cn, zhgle@ecut.edu.cn

Abstract

Visible-light-induced EDA complex-promoted ring-opening of cycloketone oxime esters to synthesise various cyanoalkylated products with N-methacryloyl benzamides was developed. Various radical receptors were compatible with the current reaction system to furnish diverse heterocyclic compounds. Mechanistic analysis shows that the formation of an EDA complex was crucial to the photocatalytic strategy. Importantly, 4-cyanoalkyl isoquinoline-1,3-diones were obtained in high yields by using a catalytic amount of 1,4-diazabicyclo[2.2.2]octane (DABCO) through prolonging the reaction time, which provided a practical approach to give a variety of isoquinoline-1,3-dione derivatives.

Graphical abstract: Visible-light-driven EDA complex-promoted cascade cyclization to construct 4-cyanoalkyl isoquinoline-1,3-diones

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Article information

DOI
https://doi.org/10.1039/D4CC00092G
Article type
Communication
Submitted
07 Jan 2024
Accepted
08 Feb 2024
First published
12 Feb 2024

Chem. Commun., 2024,60, 2958-2961

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Visible-light-driven EDA complex-promoted cascade cyclization to construct 4-cyanoalkyl isoquinoline-1,3-diones

D. Zhang, Z. Le, Q. Li, Z. Xie, W. Yang and Z. Zhu, Chem. Commun., 2024, 60, 2958 DOI: 10.1039/D4CC00092G

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