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An efficient one-pot synthesis of novel 6-hydroxy-14-aryl-8H-dibenzo[a,i]xanthene-8,13(14H)-diones derived from lawsone

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Abstract

An efficient and convenient procedure for the synthesis of novel 6-hydroxy-14-aryl-8H-dibenzo[a,i]xanthene-8,13(14H)-dione derivatives has been developed by one-pot, three-component condensation reaction between 2-hydroxynaphthalene-1,4-dione, aromatic aldehydes and 2,3-naphthalenediol in glacial acetic acid under reflux conditions. This domino reaction implies Knoevenagel condensation, Michael addition, intramolecular cyclization and dehydration. The reaction avoids tedious workup procedure due to the direct precipitation of products from the reaction medium. The notable features of this domino transformation are operational simplicity, clean reaction, easy handling, easy purification process and high yields of the products.

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Acknowledgments

The authors thank the Research Council of Payame Noor University for financial support.

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Authors and Affiliations

  1. Department of Chemistry, Payame Noor University (PNU), PO BOX, 19395-4697, Tehran, Iran

    Abolfazl Olyaei, Alireza Adl & Esmail Vessally

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  1. Abolfazl Olyaei
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  2. Alireza Adl
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  3. Esmail Vessally
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Correspondence to Abolfazl Olyaei.

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Olyaei, A., Adl, A. & Vessally, E. An efficient one-pot synthesis of novel 6-hydroxy-14-aryl-8H-dibenzo[a,i]xanthene-8,13(14H)-diones derived from lawsone. Res Chem Intermed 47, 2207–2216 (2021). https://doi.org/10.1007/s11164-021-04409-7

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