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Introduction of bis-imidazolium dihydrogen phosphate as a new green acidic ionic liquid catalyst in the synthesis of arylidene malononitrile, ethyl (E)-3-(aryl)-2-cyanoacrylate and tetrahydrobenzo[b]pyran derivatives

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Abstract

In this work, [H2-Bisim][H2PO4]2 as a novel bis-imidazole-based acidic ionic liquid has been synthesized and characterized with a variety of techniques including FT-IR, 1H, 13C, 31P NMR and mass spectroscopy techniques. After characterization, this compound was used as an affordable and recyclable catalyst in the synthesis of arylidene malononitrile, ethyl (E)-3-(aryl)-2-cyanoacrylate and tetrahydrobenzo[b]pyran derivatives. The procedure had several advantages such as excellent yields, short reaction times, simple workup and use of a non-expensive and non-toxic compound as the catalyst. Moreover, the prepared ionic liquid could be recycled and reused without significant loss in its catalytic activity in the studied reactions.

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Acknowledgements

We are thankful to the Research Council of the University of Guilan for the partial support of this research.

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Authors and Affiliations

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

    Zahra Rahmatizadeh-Pashaki & Farhad Shirini

  2. Department of Chemistry, University Campus 2, University of Guilan, Rasht, Iran

    Nader Daneshvar

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  1. Zahra Rahmatizadeh-Pashaki
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Correspondence to Farhad Shirini.

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Rahmatizadeh-Pashaki, Z., Daneshvar, N. & Shirini, F. Introduction of bis-imidazolium dihydrogen phosphate as a new green acidic ionic liquid catalyst in the synthesis of arylidene malononitrile, ethyl (E)-3-(aryl)-2-cyanoacrylate and tetrahydrobenzo[b]pyran derivatives. J IRAN CHEM SOC 18, 2135–2149 (2021). https://doi.org/10.1007/s13738-021-02177-0

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