Copper-Catalyzed 6-endo-dig O-Cyclization of 2-(But-3-en-1-yn-1-yl)benzamide

Rui-Xiang Wang; Zhuang Fang; Guanyinsheng Qiu; Wenlin Xie; Jin-Biao Liu

doi:10.1055/s-0039-1690155

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(21): 4048-4065
DOI: 10.1055/s-0039-1690155

paper

Copper-Catalyzed 6-endo-dig O-Cyclization of 2-(But-3-en-1-yn-1-yl)benzamide

Rui-Xiang Wang∗

^aDepartment of chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, P. R. of China eMail: liujinbiao@jxust.edu.cn

,

Zhuang Fang

^aDepartment of chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, P. R. of China eMail: liujinbiao@jxust.edu.cn

,

Guanyinsheng Qiu ∗

^bCollege of Biological, Chemical Science and Engineering, Jiaxing University, 118 Jiahang Road, Jiaxing 314001, P. R. of China eMail: qiuguanyinsheng@mail.zjxu.edu.cn

,

Wenlin Xie

^cSchool of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Hunan 411201, P. R. of China

,

Jin-Biao Liu ∗

^aDepartment of chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, P. R. of China eMail: liujinbiao@jxust.edu.cn

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Abstract

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Abstract

The copper-catalyzed synthesis of 3-vinylisocoumarin-1-imine is reported. The transformation proceeds smoothly with good yields in THF and the regioselectivity was determined by a O-nucleophilic 6-endo cyclization. Studies on the mechanism indicate that copper trifluoroacetate serves as a Lewis acid, and the use of vinyl-connected 2-alkynylbenzamide is important for this O-nucleophilic 6-endo cyclization.

Key words

copper catalysis - O-nucleophilic 6-endo cyclization - Lewis acid - vinyl-connected 2-alkynylbenzamide - isocoumarin

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Referenzen

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11 CCDC 1941980 contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

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