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A general and inexpensive protocol for the nanomagnetic 5-sulfosalicylic acid catalyzed the synthesis of tetrahydrobenzo[b]pyrans and quinoxaline derivatives

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Abstract

In this study, a novel acid-functionalized magnetic nanoparticles with high loaded multifunctional acidic groups was fabricated by anchoring water-soluble 5-sulfosalicylic acid onto the surface silica-modified Fe3O4. The magnetically recyclable Fe3O4@SiO2@5-SA (20 mg) showed excellent reactivity for greener synthesis of tetrahydrobenzo[b]pyrans via a three-component reaction of different aromatic aldehydes, malononitrile and dimedone in good to excellent yields (70–95%) in pure water at short reaction times (40–150 min). The method shows eco-friendly synthesis of quinoxaline derivatives from direct condensation of substituted 1,2-diamine with various 1,2-dicarbonyl in ethanol at room temperature to afford the desired quinoxalines with good to excellent yields (60–97%) at shorter reaction times (120–240 min). The morphology and magnetic properties of MNPs were studied with scanning electron microscopy, X-ray powder diffraction, Fourier translation infrared spectroscopy, vibrating sample magnetometer and thermogravimetric. The results showed that the Fe3O4@SiO2@5-SA catalyst is completely recoverable by an external magnet and retained catalytic activity after five recycles.

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Acknowledgements

The financial support of this work provided by CCERCI is gratefully appreciated.

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Authors and Affiliations

  1. Department of Chemistry, Science and Research Branch, Islamic Azad University, Tehran, Iran

    Farzaneh Saboury, Zohreh Mirjafari & Mohammad Mahmoudi Hashemi

  2. Chemistry and Chemical Engineering Research Center of Iran, P.O. Box 14335-186, Tehran, Iran

    Najmedin Azizi

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  1. Farzaneh Saboury
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  2. Najmedin Azizi
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  3. Zohreh Mirjafari
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  4. Mohammad Mahmoudi Hashemi
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Correspondence to Najmedin Azizi.

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Saboury, F., Azizi, N., Mirjafari, Z. et al. A general and inexpensive protocol for the nanomagnetic 5-sulfosalicylic acid catalyzed the synthesis of tetrahydrobenzo[b]pyrans and quinoxaline derivatives. J IRAN CHEM SOC 17, 2533–2543 (2020). https://doi.org/10.1007/s13738-020-01948-5

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