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Synthesis 2019; 51(17): 3345-3355
DOI: 10.1055/s-0037-1611837
DOI: 10.1055/s-0037-1611837
paper
One-Pot Synthesis of Trifluoromethylated Pyrazol-4-yl-pyrrole-2,5-dione Derivatives
The authors thank the National Natural Science Foundation of China (No. 21272153), and the Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry for financial support.Further Information
Publication History
Received: 18 March 2019
Accepted after revision: 29 April 2019
Publication Date:
21 May 2019 (online)
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 bondSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1611837.
- Supporting Information
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