One-Pot Synthesis of Trifluoromethylated Pyrazol-4-yl-pyrrole-2,5-dione Derivatives

Fangchong Yuan; Wenwen Duan; Zeyu Li; Xi Luo; Min Zhang; Hongmei Deng; Liping Song

doi:10.1055/s-0037-1611837

Synthesis, Table of Contents

Synthesis 2019; 51(17): 3345-3355
DOI: 10.1055/s-0037-1611837

paper

One-Pot Synthesis of Trifluoromethylated Pyrazol-4-yl-pyrrole-2,5-dione Derivatives

Fangchong Yuan

^aDepartment of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China Email: lpsong@shu.edu.cn

,

Wenwen Duan

^aDepartment of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China Email: lpsong@shu.edu.cn

,

Zeyu Li

^aDepartment of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China Email: lpsong@shu.edu.cn

,

Xi Luo

^aDepartment of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China Email: lpsong@shu.edu.cn

,

Min Zhang

^aDepartment of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China Email: lpsong@shu.edu.cn

,

Hongmei Deng

^bLaboratory for Microstructures, Shanghai University, Shanghai 200444, P. R. of China

,

Liping Song*

^aDepartment of Chemistry, School of Science, Shanghai University, No. 99, Shangda Road, Shanghai 200444, P. R. of China Email: lpsong@shu.edu.cn

^cKey Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Road, Shanghai 200032, P. R. of China

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Abstract

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Abstract

Efficient and convenient one-pot, three-component reactions of pyrrolidone, aromatic aldehydes and 1-phenyl-3-trifluoromethyl-5-pyrazolone afforded highly functionalized trifluoromethylated pyrazol-4-ylpyrrole-2,5-dione derivatives in good yields. The effect of solvents on the reaction efficiency and yield was briefly investigated. The structures of products were determined by spectral methods and X-ray diffraction analysis. The latter showed that the products formed have a strong intramolecular hydrogen bond, which made them particularly stable and the corresponding annulated products were not obtained by treatment with dehydrating reagents.

Key words

fluorinated heterocycles - multicomponent reactions - pyrrolidone - Michael addition - hydrogen bond

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References

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14 CCDC 1902835 (4a) contains the supplementary crystallographic data for this paper. The data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/getstructures.

Supplementary Material

Supporting Information