Skip to main content
SpringerLink
Log in

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

  • Published:
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.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Fig. 1

Similar content being viewed by others

Notes

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

References

  1. A. N. Nikitina, A. E. Shchekotikhin, Yu. N. Luzikov, A. M. Korolev, V. N. Buyanov, and M. N. Preobrazhenskaya, Khim. Geterotsikl. Soedin., 245 (2011). [Chem. Heterocycl. Comp., 47, 245 (2011)].

    Google Scholar 

  2. A. E. Shchekotikhin, E. K. Shevtsova, and V. F. Traven’, Zh. Org. Khim., 43, 1687 (2007).

    Google Scholar 

  3. A. E. Shchekotikhin, Yu. N. Luzikov, V. N. Buyanov, and M. N. Preobrazhenskaya, Khim. Geterotsikl. Soedin., 191 (2009). [Chem. Heterocycl. Comp., 45, 191 (2009)].

    Google Scholar 

  4. A. E. Shchekotikhin, V. A. Glazunova, L. G. Dezhenkova, E. K. Shevtsova, V. F. Traven’, J. Balzarini, H.-S. Huang, A. A. Shtil, and M. N. Preobrazhenskaya, J. Eur. Med. Chem., 46, 423 (2011).

    Article  CAS  Google Scholar 

  5. A. E. Shchekotikhin, Yu. N. Luzikov, V. N. Buyanov, and M. N. Preobrazhenskaya, Khim. Geterotsikl. Soedin., 538 (2007). [Chem. Heterocycl. Comp., 43, 538 (2007)].

    Google Scholar 

  6. M. J. Miller and G. M. Loudon, J. Org. Chem., 40, 126 (1975).

    Article  CAS  Google Scholar 

  7. M. R. Snyder, J. Org. Chem., 39, 3343 (1974).

    Article  Google Scholar 

  8. J. A. Joule and K. Mills, in: M. A. Yurovskaya (editor), Chemistry of Heterocyclic Compounds [Russian translation], Khimiya, Moscow (2004), p. 563.

    Google Scholar 

  9. P. Emmott and R. Livingstone, J. Chem. Soc., 3144 (1957).

  10. J. A. Marshall and R. E. Conrow, J. Am. Chem. Soc., 105, 5679 (1983).

    Article  CAS  Google Scholar 

  11. R. B. Gammill and S. A. Nash, J. Org. Chem., 51, 3116 (1986).

    Article  CAS  Google Scholar 

  12. G. Lamotte, P. Demerseman, and R. Royer, Synthesis, 1068 (1984).

  13. W. R. Boehme, Org. Synth., 33, 43 (1953).

    CAS  Google Scholar 

  14. T. Horaguchi, S. Matsuda, and T. Suzuki, J. Heterocycl. Chem., 24, 965 (1987).

    Article  CAS  Google Scholar 

Download references

Author information

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
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. E. Shchekotikhin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yu. N. Luzikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. M. Korolev
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. N. Preobrazhenskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

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.

Rights and permissions

Reprints and permissions

About this article

Cite this article

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

Download citation

  • Received:

  • Published:

  • Issue Date:

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

Keywords

Search

Navigation