ZnBr2/Oxone-mediated ipso-cyclization of N-(3-phenylprop-2-yn-1-yl)aniline

Keke Huang; Jia-Ni Li; Guanyinsheng Qiu; Wenlin Xie; Jin-Biao Liu

doi:10.1039/C9RA06646B

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ZnBr₂/Oxone-mediated ipso-cyclization of N-(3-phenylprop-2-yn-1-yl)aniline†

Keke Huang,^a Jia-Ni Li,^b Guanyinsheng Qiu,

*^bd Wenlin Xie^c and Jin-Biao Liu

*^a

Author affiliations

* Corresponding authors

^a School of Metallurgical and Chemical Engineering, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 341000, China
E-mail: liujinbiao@jxust.edu.cn

^b College of Biological, Chemical Science and Engineering, Jiaxing University, 118 Jiahang Road, Jiaxing 314001, China
E-mail: qiuguanyinsheng@mail.zjxu.edu.cn

^c School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, China

^d Department of Chemistry, Fudan Unversity, Shanghai, China

Abstract

In this work, a selective synthetic strategy towards 1-azaspiro[4.5]deca-3,6,9-trien-8-ones from N-tosyl-N-(prop-2-yn-1-yl)aniline is developed. The transformation proceeds smoothly in a mixed solvent including acetonitrile and water when ZnBr₂ and Oxone are employed. Mechanism studies show that the reaction proceeds in a regioselective manner via a radical ipso-cyclization pathway.

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Article information

DOI: https://doi.org/10.1039/C9RA06646B
Article type: Paper
Submitted: 23 Aug 2019
Accepted: 12 Oct 2019
First published: 17 Oct 2019
This article is Open Access

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RSC Adv., 2019,9, 33460-33464

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ZnBr₂/Oxone-mediated ipso-cyclization of N-(3-phenylprop-2-yn-1-yl)aniline

K. Huang, J. Li, G. Qiu, W. Xie and J. Liu, RSC Adv., 2019, 9, 33460 DOI: 10.1039/C9RA06646B

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