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Synthesis of novel pyrano[2,3-f]chromene-dione derivatives using phosphoric acid-functionalized silica-coated Fe3O4 nanoparticles as a new reusable solid acid nanocatalyst

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Abstract

In this research, the synthesis of novel indeno[1,2-b]pyrano[2,3-f]chromene-2,12(13H)-dione derivatives in the presence of a newly introduced magnetically recoverable nanosolid acid catalyst is reported. At the first, phosphoric acid-functionalized silica-coated Fe3O4 nanoparticles (Fe3O4@SiO2–(CH2)3OPO3H2) were prepared and well characterized using infrared spectroscopy (FT-IR), X-ray diffraction (XRD), scanning electron microscopy (SEM), vibrating sample magnetometer (VSM), and energy-dispersive X-ray spectroscopy (EDS) techniques. Then, the catalytic activity of the prepared Fe3O4@ SiO2–(CH2)3OPO3H2 nanocatalyst was investigated for the synthesis of novel indeno[1,2-b]pyrano[2,3-f]chromene-2,12(13H)-dione derivatives via a one-pot and three-component condensation between 5,7-dihydroxy-4-methylcoumarin, indane-1, 3-dione, and various aromatic aldehydes under solvent-free condition. All the products are unknown, and their characterization was performed with the spectral data information obtained from their FT-IR, 1H and 13CNMR, elemental analysis, and their melting points. The reusability study of the introduced nanosolid acid catalyst showed that the catalytic stability is almost completely remained up to five consecutive runs.

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Acknowledgements

The authors gratefully acknowledge the partial support of this work by Yasouj University, Yasouj, Iran.

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Authors and Affiliations

  1. Department of Chemistry, Yasouj University, P. O. Box 353, 75918-74831, Yasouj, Iran

    Iman Sedighimehr, Bahador Karami & Mahnaz Farahi

  2. Department of Applied Chemistry, Faculty of Gas and Petroleum, Yasouj University, Gachsaran, Iran

    Mosadegh Keshavarz

Authors
  1. Iman Sedighimehr
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  2. Bahador Karami
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  3. Mahnaz Farahi
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  4. Mosadegh Keshavarz
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Correspondence to Bahador Karami.

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Sedighimehr, I., Karami, B., Farahi, M. et al. Synthesis of novel pyrano[2,3-f]chromene-dione derivatives using phosphoric acid-functionalized silica-coated Fe3O4 nanoparticles as a new reusable solid acid nanocatalyst. Mol Divers 26, 3325–3336 (2022). https://doi.org/10.1007/s11030-022-10393-w

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  • DOI: https://doi.org/10.1007/s11030-022-10393-w

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