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Facile One-Pot Synthesis of Flavanones Using Tetramethylguanidinum-Based Ionic Liquids as Catalysts

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Abstract

Several tetramethylguanidinum-based ionic liquids (TMGILs) were prepared, characterized and used as catalysts in one-pot synthesis of flavanones. The results indicated that TMGILs composed of phenolate anion was beneficial for one-pot synthesis of flavanones, and [TMG][4-MeO–PhO] induced the good yields of flavanones owing to the electron-donating effect of methoxy substituent on phenolate anion. Furthermore, [TMG][4-MeO–PhO] was found to be used repetitively at least five times without obvious decrease in activity and quantity.

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Acknowledgments

We thank the financial support by the National Natural Science Foundations of China (No. 21206063), the Department of Science and Technology of Jiangxi Province (Nos. 20151BAB213016, 20123BBE50081, 20132BDH80003), and the Sponsored Program for Cultivating Youths of Outstanding Ability in Jiangxi Normal University.

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Authors and Affiliations

  1. Key Laboratory of Functional Small Organic Molecules, Ministry of Education, College of Chemistry and Chemical Engineering, Center of Analysis and Testing, Jiangxi Normal University, Nanchang, 330022, People’s Republic of China

    Yan Zhou, Wei Huang, Xiang-Shu Chen, Zhi-Bin Song & Duan-Jian Tao

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  1. Yan Zhou
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  2. Wei Huang
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  3. Xiang-Shu Chen
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  4. Zhi-Bin Song
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  5. Duan-Jian Tao
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Correspondence to Xiang-Shu Chen or Zhi-Bin Song.

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Zhou, Y., Huang, W., Chen, XS. et al. Facile One-Pot Synthesis of Flavanones Using Tetramethylguanidinum-Based Ionic Liquids as Catalysts. Catal Lett 145, 1830–1836 (2015). https://doi.org/10.1007/s10562-015-1581-9

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  • DOI: https://doi.org/10.1007/s10562-015-1581-9

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