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Heterocyclic Analogs of 5,12-Naphthacene-Quinone. 12. Synthesis of 2-Substituted Derivatives of 4,11-Dimethoxy-5,10-Dioxo-Anthra[2,3-b]Furan-3-Carboxylic Acids

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Chemistry of Heterocyclic Compounds Aims and scope

The synthesis of anthrafurandiones, by means of which it is possible to obtain a series of previously unknown 2-substituted derivatives of 4,11-dimethoxy-5,10-dioxoanthra[2,3-b]furan-3-carboxylic acids after protection of the hydroxy groups of the initial 2,3-dibromoquinizarin, was optimized. Unlike most of the analogs, 4,11-dimethoxy-5,10-dioxo-2-(trifluoromethyl)anthra[2,3-b]furan-3-carboxylic acid ester is best synthesized from 2,3-dibromoquinizarin with subsequent methylation of the hydroxy groups. The heterocyclic ring of this ester was found to have low stability during the action of alkalis. This, together with the side deacetylation of the intermediate, is probably the main reason for its low yield at the heterocyclization stage.

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Notes

  1. Here and subsequently all the signals without assignments in the 13C NMR spectra belong to the quaternary carbon atoms.

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The work was carried out with financial support from the Ministry of Industry and Trade of the Russian Federation (state contract 12411.1008799.13.007).

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Authors and Affiliations

  1. Gause Institute of New Antibiotics, Russian Academy of Medical Sciences, 11 B. Pirogovskaya St., Moscow, 119021, Russia

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

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

    A. S. Tikhomirov & A. E. Shchekotikhin

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 11, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 2, pp. 298-308, February, 2014.

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Tikhomirov, A.S., Shchekotikhin, A.E., Luzikov, Y.N. et al. Heterocyclic Analogs of 5,12-Naphthacene-Quinone. 12. Synthesis of 2-Substituted Derivatives of 4,11-Dimethoxy-5,10-Dioxo-Anthra[2,3-b]Furan-3-Carboxylic Acids. Chem Heterocycl Comp 50, 271–280 (2014). https://doi.org/10.1007/s10593-014-1471-x

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