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Synthesis
DOI: 10.1055/a-2517-1556
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Metal-free Photo-Induced Cascade Cyclization of Alkyne-Tethered N-Alkoxylbenzamides

Ximei Tang
1   Chemistry, Jiaxing University, Jiaxing, China (Ringgold ID: RIN66559)
,
Chen Bao
2   School of Urban construction, Jiaxing Vocational and Technical College, Jiaxing, China (Ringgold ID: RIN216802)
,
Guang Cheng
1   Chemistry, Jiaxing University, Jiaxing, China (Ringgold ID: RIN66559)
,
Yuling Liao
1   Chemistry, Jiaxing University, Jiaxing, China (Ringgold ID: RIN66559)
,
Wenlin Xie
3   School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, China (Ringgold ID: RIN12518)
,
Guanyinsheng Qiu
4   College of Biological, Chemical Science and Engineering, Jiaxing University, Jiaxing, China (Ringgold ID: RIN66559)
› Author AffiliationsSupported by: Natural Science Foundation of Zhejiang Province LQ22B020006
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In this work, a photo-induced synthesis of isoxazolidine-fused isoquinolin-1-ones and 3,4-dihydro-[1,2]oxazino[2,3-b]isoquinolin-10(2H)-one from alkyne-tethered N-alkoxybenzamides is reported. The gram-scaled synthesis and structural elaboration of isoxazolidine-fused isoquinolin-1-one are also realized. The reaction is promoted by 1.0 equiv of TBAC, featuring with metal-free and catalyst-free conditions. In the reaction, it is believed that the starting materials alkyne-tethered N-alkoxybenzamides serve as photo-sensitizer, and the photoexcited substrate induces the formation of chloro radical. The N-radical results from hydrogen atom abstraction of chloro radical with N-H bond of substrates.



Publication History

Received: 17 December 2024

Accepted after revision: 15 January 2025

Accepted Manuscript online:
15 January 2025

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