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Comparison of the efficiency of two imidazole-based dicationic ionic liquids as the catalysts in the synthesis of pyran derivatives and Knoevenagel condensations

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Abstract

In the present work, 3,3′-(butane-1,4-diyl)bis(1-methyl-1H-imidazol-3-ium) dichloride ([C4(MIm)2]·2Cl) and 3,3′-(butane-1,4-diyl)bis(1-methyl-1H-imidazol-3-ium) hydrogen sulfate ([C4(MIm)2]·2HSO4) were prepared via adequate, solvent-free methods and characterized using FT-IR, 1H NMR, 13C NMR, and potentiometric titration techniques. These reagents were investigated in the synthesis of 5-arylidene (thio)barbituric acids, 2-arylidene malononitriles, 4H-pyrans, and pyrano[2,3-d] pyrimidineones, and their catalytic activities were compared in the promotion of these reactions. Based on the obtained results, we found that [C4(MIm)2]·2Cl showed more catalytic efficiency where a basic or weak acidic media is needed. In contrast, [C4(MIm)2]·2HSO4 is a powerful catalyst in reactions needing acidic catalysts to enhance the reaction rate. Using these reagents, the products were formed under mild and eco-friendly conditions in excellent yields during short reaction times without needing column chromatography for work-up.

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Acknowledgements

Facilitation of the studies by the University of Guilan Research Council is appreciably acknowledged.

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Authors and Affiliations

  1. Department of Chemistry, College of Science, University of Guilan, University Campus 2, 41335-19141, Rasht, Iran

    Zahra Sharifi, Nader Daneshvar, Mohaddeseh Safarpoor Nikoo Langarudi & Farhad Shirini

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  1. Zahra Sharifi
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Sharifi, Z., Daneshvar, N., Langarudi, M.S.N. et al. Comparison of the efficiency of two imidazole-based dicationic ionic liquids as the catalysts in the synthesis of pyran derivatives and Knoevenagel condensations. Res Chem Intermed 45, 4941–4958 (2019). https://doi.org/10.1007/s11164-019-03874-5

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