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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

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
› Author AffiliationsThe authors are grateful to the National Natural Science Foundation of China (Grant Nos. 21672138, 21542005, 21272152) for their financial support.
Further Information

Publication History

Received: 28 April 2018

Accepted after revision: 31 May 2018

Publication Date:
23 July 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

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610443.
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