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Two Novel Pyrazole Derived Ionic Liquids Based on Chloride and Trichlorostannate Anions: Preparation, Characterization, and Evaluation of Their Catalytic Activity in the Synthesis of 1H-Pyrazolo[1,2-b]phthalazine-5,10-diones

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Abstract

Two novel room-temperature disulfonic acid functionalized ionic liquids derived from 3,5-dimethyl-1H-pyrazole consisting of chloride and trichlorostannate anions, 3,5-dimethyl-1,2-disulfonic acid-1H-pyrazolium chloride and 3,5-dimethyl-1,2-disulfonic acid-1H-pyrazolium trichlorostannate, have been synthesized, characterized and evaluated for their catalytic efficiency in the synthesis of 1H-pyrazolo[1,2-b]phthalazine-5,10-diones by the one-pot, three-components reaction of phthalhydrazide, an aromatic aldehyde and malononitrile or ethyl cyanoacetate under solvent-free conditions. The results have demonstrated high catalytic activity of these novel ionic liquids containing acidic SO3H groups in producing high yields of the desired products in short reaction time. The ionic liquids can be used at least four times without any noticeable decrease in catalytic activity.

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ACKNOWLEDGMENTS

The authors express their gratitude to the Islamic Azad University, Mashhad Branch for its financial support.

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Authors and Affiliations

  1. Department of Chemistry, Mashhad Branch, Islamic Azad University, 9175687119, Mashhad, Iran

    A. Vafaee & A. Davoodnia

  2. Young Researchers and Elite Club, Mashhad Branch, Islamic Azad University, 9175687119, Mashhad, Iran

    A. Nakhaei & S. Yadegarian

  3. Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, 9177948974, Mashhad, Iran

    M. Nejatianfar

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  1. A. Vafaee
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  2. A. Davoodnia
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  3. A. Nakhaei
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  4. S. Yadegarian
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Correspondence to A. Davoodnia or A. Nakhaei.

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Vafaee, A., Davoodnia, A., Nakhaei, A. et al. Two Novel Pyrazole Derived Ionic Liquids Based on Chloride and Trichlorostannate Anions: Preparation, Characterization, and Evaluation of Their Catalytic Activity in the Synthesis of 1H-Pyrazolo[1,2-b]phthalazine-5,10-diones. Russ J Gen Chem 91, 273–278 (2021). https://doi.org/10.1134/S1070363221020158

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