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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

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
› Author AffiliationsThe 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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1609563.
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