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1H-imidazol-3-ium tricyanomethanide {[HIM]C(CN)3} as a nanostructured molten salt catalyst: application to the synthesis of pyrano[4,3‐b]pyrans

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Abstract

In this work, we have synthesized a novel nanostructured molten salt, 1H-imidazol-3-ium tricyanomethanide {[HIMI]C(CN)3} (1), as an efficient and green protocol-compatible catalyst. This new molten salt has been fully characterized by different analytical techniques, such as FT-IR, 1HNMR, 13CNMR, thermal gravimetric analysis, derivative thermal gravimetric analysis, differential thermal analysis, X-ray diffraction, scanning electron microscopy, and high-resolution transmission electron microscopy. Additionally, the catalytic activity of {[HIMI]C(CN)3} (1, 2 mol%) has been tested in a three-component domino Knoevenagel condensation reaction. A range of structurally diverse aromatic aldehydes (2a–p), malononitrile (3), and 4‐hydroxy‐6‐methyl‐2H‐pyran‐2‐one (4) are tolerated for the synthesis of 2-amino-7-methyl-5-oxo-4-aryl-4,5-dihydropyrano[4,3-b]pyran-3-carbonitrile derivatives (5a–p) under neat conditions at 50 °C. The obtained results have demonstrated that catalyst 1 shows interesting catalytic properties, such as clean reaction profile, cost-effectiveness, and green conditions. Importantly, the aforementioned catalyst is thermally stable with a 171 °C melting point not showing any significant loss in catalytic activity after 7 reaction cycles.

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  • 30 June 2020

    Since it has been cleared that a fake compound has been sold to us as cyanoform.

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Acknowledgements

We thank Bu-Ali Sina University, Iran National Science Foundation (INSF) (Grant of Allameh Tabataba’i’s Award, Grant Number BN093), National Elites Foundation, University of Alicante (VIGROB-173), and the Spanish Ministerio de Economíay Competitividad (CTQ2015-66624-P) for financial support to our research groups.

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Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, Bu-Ali Sina University, Hamedan, 6517838683, Iran

    Mohammad Ali Zolfigol, Meysam Yarie & Saeed Baghery

  2. Departamento de Química Orgánica, and Instituto de Síntesis Orgánica, Universidad de Alicante, Apdo. 99, 03080, Alicante, Spain

    Abbas Khoshnood & Diego A. Alonso

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  1. Mohammad Ali Zolfigol
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  2. Meysam Yarie
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  3. Saeed Baghery
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  4. Abbas Khoshnood
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  5. Diego A. Alonso
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Correspondence to Mohammad Ali Zolfigol, Meysam Yarie, Abbas Khoshnood or Diego A. Alonso.

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Zolfigol, M.A., Yarie, M., Baghery, S. et al. 1H-imidazol-3-ium tricyanomethanide {[HIM]C(CN)3} as a nanostructured molten salt catalyst: application to the synthesis of pyrano[4,3‐b]pyrans. Res Chem Intermed 43, 3291–3305 (2017). https://doi.org/10.1007/s11164-016-2826-y

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