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Preparation, characterization, and use of poly(vinylpyrrolidonium) hydrogen phosphate ([PVP-H]H2PO4) as a new heterogeneous catalyst for efficient synthesis of 2-amino-tetrahydro-4H-pyrans

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Abstract

A novel Brønsted solid acid named poly(vinylpyrrolidonium) hydrogen phosphate ([PVP-H]H2PO4) has been prepared by using H3PO4 and poly(vinylpyrrolidone) as green and commercially available reagents. The prepared reagent was characterized using a series of techniques including Fourier-transform infrared (FT-IR) spectroscopy, thermogravimetric analysis (TGA), scanning electron microscopy (SEM), X-ray diffraction (XRD) analysis, energy-dispersive X-ray analysis (EDAX), pH analysis, and Hammett acidity function. The mentioned solid acid with wide acidic functional group sites can be utilized as a highly efficient, heterogeneous, and reusable catalyst for preparation of 2-amino-3-cyano-5-oxo-5,6,7,8-tetrahydro-4H-benzopyrans using aldehydes, dimedone, and malononitrile. Also, this catalyst can be reused for several times without loss of catalytic activity.

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Acknowledgments

The authors are grateful to the Guilan University Research Council for partial support of this work.

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Authors and Affiliations

  1. Department of Chemistry, College of Science, University of Guilan, Post Box 1914, Rasht, 41335, I. R. Iran

    Farhad Shirini, Omid Goli-Jolodar & Mohadeseh Seddighi

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

    Maryam Akbari

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  1. Farhad Shirini
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  2. Omid Goli-Jolodar
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  3. Maryam Akbari
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  4. Mohadeseh Seddighi
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Correspondence to Farhad Shirini.

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Shirini, F., Goli-Jolodar, O., Akbari, M. et al. Preparation, characterization, and use of poly(vinylpyrrolidonium) hydrogen phosphate ([PVP-H]H2PO4) as a new heterogeneous catalyst for efficient synthesis of 2-amino-tetrahydro-4H-pyrans. Res Chem Intermed 42, 4733–4749 (2016). https://doi.org/10.1007/s11164-015-2312-y

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