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. 2019 Oct 17;9(57):33460-33464.
doi: 10.1039/c9ra06646b. eCollection 2019 Oct 15.

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

Keke Huang  1 , Jia-Ni Li  2 , Guanyinsheng Qiu  2   3 , Wenlin Xie  4 , Jin-Biao Liu  1
Affiliations

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

Keke Huang et al. RSC Adv. .

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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Conflict of interest statement

There are no conflicts to declare.

Figures

Scheme 1
Scheme 1. Proposed route for the synthesis of trienones.
Scheme 2
Scheme 2. Proposed mechanism.
See this image and copyright information in PMC

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