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A new efficient synthesis of highly functionalized alizarins from alizarin, acetylenic esters, and isocyanides

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Abstract

The reactive intermediates generated by the addition of isocyanides to dialkyl acetylenedicarboxylates were trapped by alizarin to produce dialkyl 2-alkyl (aryl) amino-6,11-dihydro-12-hydroxy-6,11-dioxo-4H-naphtho [2,3-g]chromene-3,4-dicarboxylates in good yields. When the reactions were carried out in the presence of ethyl propiolate as acetylenic component, ethyl 4-alkyl (aryl) imino-4-(9,10-dihydro-1-hydroxy-9,10-dioxoanthracen-2-yloxy)but-2-enoates were obtained.

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Acknowledgments

We are grateful to Professor Issa Yavari for discussions and to East Tehran Branch, Islamic Azad University for financial support.

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Authors and Affiliations

  1. Department of Chemistry, College of Basic Science, East Tehran Branch, Islamic Azad University, Tehran, Iran

    Leila Azad

  2. Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran

    Haleh Sanaeishoar

  3. Department of Chemistry, University of Tarbiat Modares, Tehran, Iran

    Issa Yavari

Authors
  1. Leila Azad
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  2. Haleh Sanaeishoar
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  3. Issa Yavari
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Correspondence to Leila Azad.

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Azad, L., Sanaeishoar, H. & Yavari, I. A new efficient synthesis of highly functionalized alizarins from alizarin, acetylenic esters, and isocyanides. Monatsh Chem 147, 1251–1256 (2016). https://doi.org/10.1007/s00706-015-1643-0

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  • DOI: https://doi.org/10.1007/s00706-015-1643-0

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