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Synthesis 2018; 50(18): 3731-3737
DOI: 10.1055/s-0037-1610443
paper
© Georg Thieme Verlag Stuttgart · New York

[3+2] Cycloaddition of N-Aminopyridines and Perfluoroalkynylphosphonates: Facile Synthesis of Perfluoroalkylated Pyrazolo[1,5-a]pyridines Containing a Phosphonate Moiety

Authors

  • Qi Huang

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

  • Dong He

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

  • Jing Han

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

  • Jie Chen

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

  • Weimin He

    a   Department of Chemistry, Innovative Drug Research Center, Shanghai University, Shanghai 200444, P. R. of China   eMail: yehao7171@shu.edu.cn   eMail: wgcao@staff.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: yehao7171@shu.edu.cn   eMail: wgcao@staff.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: yehao7171@shu.edu.cn   eMail: wgcao@staff.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 (Grant Nos. 21672138, 21542005, 21272152) for their financial support.
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Publikationsverlauf

Received: 28. April 2018

Accepted after revision: 31. Mai 2018

Publikationsdatum:
23. Juli 2018 (online)

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§ With equal contribution to this work.

Abstract

1,3-Zwitterions generated from N-aminopyridines in the presence of base are trapped by perfluoroalkynylphosphonates to yield a variety of perfluoroalkylated pyrazolo[1,5-a]pyridine derivatives bearing a phosphonate group. The salient features of these [3+2] cycloadditions include operational simplicity, good tolerance of functional groups, and good to excellent yields at room temperature.

Key words

N-aminopyridine - perfluoroalkynylphosphonate - pyrazolo[1,5-a]pyridine - [3+2] cycloaddition - synthetic methodology

Supporting Information