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Synthesis 2017; 49(06): 1356-1370
DOI: 10.1055/s-0036-1588655
paper
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Tricyclic Isoxazoles via Sequential [3+2] Dipolar Cycloaddition­ and Palladium-Catalyzed Intramolecular Arylation Reactions

Dong-Cai Guo
College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Dandong Lu West 1, Fushun 113001, P. R. of China   Email: yupeng.he@lnpu.edu.cn   Email: fang.yu@lnpu.edu.cn
,
Chao Zhang
College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Dandong Lu West 1, Fushun 113001, P. R. of China   Email: yupeng.he@lnpu.edu.cn   Email: fang.yu@lnpu.edu.cn
,
Fei Li
College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Dandong Lu West 1, Fushun 113001, P. R. of China   Email: yupeng.he@lnpu.edu.cn   Email: fang.yu@lnpu.edu.cn
,
Fenghua Zhang
College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Dandong Lu West 1, Fushun 113001, P. R. of China   Email: yupeng.he@lnpu.edu.cn   Email: fang.yu@lnpu.edu.cn
,
Fang Yu*
College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Dandong Lu West 1, Fushun 113001, P. R. of China   Email: yupeng.he@lnpu.edu.cn   Email: fang.yu@lnpu.edu.cn
,
Yu-Peng He*
College of Chemistry, Chemical Engineering and Environmental Engineering, Liaoning Shihua University, Dandong Lu West 1, Fushun 113001, P. R. of China   Email: yupeng.he@lnpu.edu.cn   Email: fang.yu@lnpu.edu.cn
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Further Information

Publication History

Received: 20 August 2016

Accepted after revision: 27 October 2016

Publication Date:
01 December 2016 (online)

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Abstract

An efficient synthetic route to tricyclic isoxazoles via sequential copper-catalyzed 1,3-dipolar cycloaddition and palladium-catalyzed intramolecular arylation of isoxazoles is described. Based on these reactions, a convenient one-pot synthesis of the tricyclic isoxazoles from terminal alkyne and hydroximoyl chlorides by using a cascade process was also developed.

Key words

isoxazoles - C–H activation - 1,3-dipolar cycloaddition - intramolecular arylation - tandem processes

Supporting Information

    Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588655.
  • Supporting Information
 

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