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Synthesis 2018; 50(23): 4668-4682
DOI: 10.1055/s-0037-1609563
paper
© Georg Thieme Verlag Stuttgart · New York

N-Heterocycle-Triggered MCRs: An Approach to the Concise Synthesis of Perfluoroalkylated Spiro-1,3-oxazines

Authors

  • Gang Liu

    a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn

  • Yueci Wu

    a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn

  • Jing Han

    a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn

  • Weimin He

    a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn

  • Jie Chen

    a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn

  • Hongmei Deng

    b   Laboratory for Microstructures and Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. of China

  • Min Shao

    b   Laboratory for Microstructures and Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. of China

  • Hui Zhang*

    a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn
    b   Laboratory for Microstructures and Instrumental Analysis and Research Center, Shanghai University, Shanghai 200444, P. R. of China

  • Weiguo Cao*

    a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   Email: wgcao@staff.shu.edu.cn   Email: yehao7171@shu.edu.cn
    c   State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China
    d   Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. of China

The authors are grateful to the National Natural Science Foundation of China (NSFC) (Grant No. 21672138, 21542005, 21272152) for the financial support.
Further Information

Publication History

Received: 07 May 2018

Accepted after revision: 29 June 2018

Publication Date:
08 August 2018 (online)

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Abstract

Multicomponent reactions involving methyl perfluoroalk-2-ynoates initiated by N-heterocycles (quinoline, isoquinoline, and benzothiazole) in the presence of isatins and diaryl 1,2-diketones allowed efficient access to trifluoromethyl- or other perfluoroalkyl-substituted spiro-1,3-oxazine derivatives. This facile transformation is regioselective and proceeded smoothly through a 1,4-dipolar intermediate under mild conditions, affording the products in good to excellent yields.

Key words

multicomponent reaction (MCR) - N-heterocycle - 1,4-dipole - perfluoroalkyl-substituted - spiro-oxazino derivatives

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