Synthesis 2019; 51(21): 4048-4065
DOI: 10.1055/s-0039-1690155
paper
© Georg Thieme Verlag Stuttgart · New York

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

Rui-Xiang Wang
a  Department of chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, P. R. of China   Email: liujinbiao@jxust.edu.cn
,
Zhuang Fang
a  Department of chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, P. R. of China   Email: liujinbiao@jxust.edu.cn
,
b  College 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
c  School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Hunan 411201, P. R. of China
,
a  Department of chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, P. R. of China   Email: liujinbiao@jxust.edu.cn
› Author Affiliations
Financial support from the National Natural Science Foundation of China (51564021, 21762018 and 21772067), the Program of Qingjiang Excellent Young Talents, Jiangxi University of Science and Technology, and the Science and Technology Innovation Outstanding Young Talents Program of Jiangxi Province (20192BCBL23009) is gratefully acknowledged.
Further Information

Publication History

Received: 21 June 2019

Accepted after revision: 23 July 2019

Publication Date:
14 August 2019 (online)

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.

Supporting Information

 
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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.