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Highly efficient synthesis of dicoumarols and xanthene derivatives in presence of Brønsted–Lewis acidic ionic liquids catalyst

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Abstract

A series of metal chloride-based acidic ionic liquids have been prepared and used as an efficient catalyst in one-pot multicomponent synthesis of biscoumarins and substituted xanthenes derivatives under solvent-free conditions. Among the acidic ionic liquids, N-methylpyrrolidonium zinc chloride (Hnmp/ZnCl3)-based Brønsted–Lewis acidic ionic liquids were found to be an effective and recyclable catalyst for a one-pot synthesis of biscoumarins through the domino Knoevenagel–Michael reaction of a variety of aldehydes with 4-hydroxycoumarin in short reaction times. The reactions which occur under relatively mild conditions afforded the biscoumarin derivatives employing a very low loading of catalyst in satisfactory isolated yields and high purity after simple work-up. The Brønsted–Lewis acidic ionic liquid catalyst was reused four times without any variation in yield.

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Acknowledgements

Financial support of this work by the Chemistry and Chemical Engineering Research Center of Iran is gratefully appreciated.

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Authors and Affiliations

  1. Department of Chemistry, Islamic Azad University-Arak Branch, P.O. Box 38135-567, Arāk, Iran

    Faezeh Abbasi & Masumeh Abdoli-Senejani

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

    Najmedin Azizi

Authors
  1. Faezeh Abbasi
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  2. Najmedin Azizi
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  3. Masumeh Abdoli-Senejani
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Correspondence to Najmedin Azizi.

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Abbasi, F., Azizi, N. & Abdoli-Senejani, M. Highly efficient synthesis of dicoumarols and xanthene derivatives in presence of Brønsted–Lewis acidic ionic liquids catalyst. J IRAN CHEM SOC 14, 2097–2103 (2017). https://doi.org/10.1007/s13738-017-1146-5

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  • DOI: https://doi.org/10.1007/s13738-017-1146-5

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