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Heterocyclic analogs of 5,12-naphthacenequinone 10.* Synthesis of furanoquinizarine and its new derivatives

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Chemistry of Heterocyclic Compounds Aims and scope

A new method was developed for synthesis of anthra[2,3-b]furan-5,10-dione derivatives. The key compound for annelation of the furan fragment to the anthraquinone chromophor is the previously unknown analog of salicylaldehyde, 1,4-dimethoxy-3-formyl-2-hydroxyanthraquinone, which we have synthesized by the Miller–Loudon–Schneider reaction. A chain of sequential transformations was used for its conversion into the target 4,11-dihydroxyanthra[2,3-b]furan-5,10-dione (furanoquinizarine): O-alkylation of the starting formylhydroxyanthraquinone with bromoacetic acid esters, cyclo-dehydration of the 3-formylanthraquinon-2-ylacetic acid esters in the presence of bases, hydrolysis of the obtained esters to 4,11-dimethoxy-5,10-dioxo-5,10-dihydroanthra[2,3-b]furan-2-carboxylic acid, its decarboxylation, and demethylation of the obtained 4,11-dimethoxyanthra[2,3-b]furan-5,10-dione.

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Notes

  1. Here and subsequently in the 13C NMR spectra all the unassigned signals belong to the quaternary carbon atoms.

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Authors and Affiliations

  1. G. F. Gauze Research Institute for New Antibiotics, Russian Academy of Medical Sciences, 11a B. Pirogovskaya St., Moscow, 119021, Russia

    A. E. Shchekotikhin, Yu. N. Luzikov, A. M. Korolev & M. N. Preobrazhenskaya

  2. D. I. Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Sq., Moscow, 125047, Russia

    A. S. Tikhomirov

Authors
  1. A. S. Tikhomirov
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  2. A. E. Shchekotikhin
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  3. Yu. N. Luzikov
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  4. A. M. Korolev
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  5. M. N. Preobrazhenskaya
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Corresponding author

Correspondence to A. E. Shchekotikhin.

Additional information

*For Communication 9, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, pp. 1464-1470, November, 2011.

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Tikhomirov, A.S., Shchekotikhin, A.E., Luzikov, Y.N. et al. Heterocyclic analogs of 5,12-naphthacenequinone 10.* Synthesis of furanoquinizarine and its new derivatives. Chem Heterocycl Comp 47, 1206–1211 (2012). https://doi.org/10.1007/s10593-012-0895-4

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  • DOI: https://doi.org/10.1007/s10593-012-0895-4

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