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Nickel(II) chromite nanoparticles promoted efficient synthesis of novel [1]benzopyrano[4,3-b]pyridines in aqueous media

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Abstract

A library of new 9,11-dimethyl-7-aryl-6H-[1]benzopyrano[3′,4′:5,6]pyrido[2,3-d]pyrimidine-6,8,10(9H,11H)triones was successfully synthesized via one-pot three-component reaction of 4-aminocoumarin, aromatic aldehydes, and 1,3-dimethylbarbituric acid using nickel(II) chromite nanoparticles as an efficient novel heterogeneous catalyst in aqueous media at 70 °C. The presented reaction is presumed to proceed via a domino Knoevenagel condensation–Michael addition, followed by intramolecular cyclization, and subsequent aromatization. The structures of the title compounds which have been successfully synthesized for the first time in this work were characterized by IR, 1H NMR, and 13C NMR spectroscopic data and also by elemental analysis. Surprisingly, the new protocol described herein provides several advantages such as high yields of products, short reaction times, mild reaction conditions, easily operated and environmentally friendly procedure. Furthermore, the catalyst can be recovered conveniently and reused without obvious loss of activity.

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Acknowledgements

We are pleased to thank Science and Research Branch, and East Tehran Branch, Islamic Azad University.

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Authors and Affiliations

  1. Department of Chemistry, Science and Research Branch, Islamic Azad University, P.O. Box 14515/775, Tehran, Iran

    Bahareh Saeedi & Zohreh Mirjafari

  2. Department of Chemistry, East Tehran Branch, Islamic Azad University, P.O. Box 18735-138, Tehran, Iran

    Shahrzad Abdolmohammadi & Reza Kia-Kojoori

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  1. Bahareh Saeedi
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  2. Shahrzad Abdolmohammadi
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  3. Zohreh Mirjafari
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  4. Reza Kia-Kojoori
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Correspondence to Shahrzad Abdolmohammadi.

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Saeedi, B., Abdolmohammadi, S., Mirjafari, Z. et al. Nickel(II) chromite nanoparticles promoted efficient synthesis of novel [1]benzopyrano[4,3-b]pyridines in aqueous media. Monatsh Chem 151, 773–780 (2020). https://doi.org/10.1007/s00706-020-02595-5

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