Skip to main content
SpringerLink
Log in

Condensation of hydroxy naphthazarins with aromatic aldehydes

  • Full Articles
  • Published:
Russian Chemical Bulletin Aims and scope

Abstract

Hydroxy naphthazarins (2,5,8-trihydroxy-1,4-naphthoquinones) react with aromatic aldehydes containing no hydroxy groups at position 2 under mild acid catalysis to form 3,3′-(arylmethylene)bisnaphthazarins. On the example of o-vanillin, it was shown that the reaction of 2-hydroxybenzaldehydes with hydroxy naphthazarins under the same conditions leads to 7,10-dihydroxy-12H-benzo[b]xanthene-6,11-dione derivatives.

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. V. F. Anufriev, A. Ya. Chizhova, V. A. Denisenko, V. L. Novikov, Zh. Org. Khim., 1993, 29, 2008 [Russ. J. Org. Chem., 1993, 29, 2008 (Engl. Transl.)].

    CAS  Google Scholar 

  2. A. Ya. Chizhova, V. F. Anufriev, V. L. Novikov, Zh. Org. Khim., 1995, 31, 237 [Russ. J. Org. Chem., 1995, 31, 237 (Engl. Transl.)].

    CAS  Google Scholar 

  3. A. Ya. Tchizhova, V. Ph. Anufriev, V. A. Denisenko, V. L. Novikov, J. Nat. Prod., 1995, 11, 1772.

    Article  Google Scholar 

  4. G. L. Bennett, L. J. Harrison, M.-Sh. Lim, K.-Y. Sim, E.-Ch. Tan, J. D. Connolly, Phytochem., 1991, 30, 3141.

    Article  CAS  Google Scholar 

  5. A. Ya. Tchizhova, V. Ph. Anufriev, V. L. Novikov, in Recent Discoveries in Natural Product Chemistry, Elite Publishers: Karachi, 1995, 101.

    Google Scholar 

  6. K. Shin-ya, S. Imai, K. Furihata, Y. Hayakawa, Y. Kato, G. D. Vanduyne, J. Clardy, H. Seto, J. Antibiot., 1990, 43, 444.

    CAS  Google Scholar 

  7. A. Ya. Chizhova, V. F. Anufriev, Zh. Org. Khim., 2000, 36, 1038 [Russ. J. Org. Chem., 2000, 36, 1007 (Engl. Transl.)].

    Google Scholar 

  8. A. Ya. Yakubovskaya, N. D. Pokhilo, V. P. Glazunov, V. F. Anufriev, G. B. Elyakov, Izv. Akad. Nauk, Ser. Khim., 2004, 2519 [Russ. Chem. Bull., Int. Ed., 2004, 53, 2626].

  9. G. I. Sopelnyak, A. Ya. Yakubovskaya, N. D. Pokhilo, V. P Glazunov, V. Ph. Anufriev, 3 rd EuroAsian Heterocyclic Meeting Heterocycles in Organic and Combinatorial Chemistry Novosibirsk, 2004, p. 204.

  10. S. Patai, The Chemistry of Quinonoid Compounds, New York, 1974, 1274 p.

  11. S. Patai, Z. Rappaport, The Chemistry of Quinonoid Compounds, New York, 1988, 1199 p.

  12. H. Ulrich, R. Richter, Die para-Chinone der Benzol- und Naphthalin-Reihe, in I. Houben, T. Weyl, Methoden der Organischen Chemie, Georg Thieme Verlag: Stuttgart, 1977, Bd. 7/3a, 832 p.

    Google Scholar 

  13. R. H. Thomson, Naturally Occurring Quinones; 3rd., Chapman & Hall; London, 1987, 732 p.

    Google Scholar 

  14. R. H. Thomson, Naturally Occurring Quinones; 4th ed., Chapman & Hall; London, 1997, 746 p.

    Google Scholar 

  15. R. H. Thomson, Naturally Occurring Quinones; 2nd ed., Acad. Press, London, 1971, p. 734.

    Google Scholar 

  16. J. W. Mathieson, R. H. Thomson, J. Chem. Soc., 1971, 153.

  17. E. A. Kol’tsova, V. A. Denisenko, O. B. Maksimov, Khim. Prirod. Soedin., 1978, 4, 438 [Chem. Nat. Comp., 1978, 4 (Engl. Transl.)].

    Google Scholar 

  18. G. V. Malinovskaya, A. Ya. Chizhova, V. F. Anufriev, Izv. Akad. Nauk, Ser. Khim., 1999, 1019 [Russ. Chem. Bull., Int. Ed., 1999, 48, 1010].

    Google Scholar 

  19. N. Donaldson, Chemistry and Technology of Compounds of the Naphthalene Series, Moscow, Goskhimizdat, 1963, p. 444.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Pacific Institute of Bioorganic Chemistry, Far-Eastern Branch of the Russian Academy of Sciences, 159 prosp. 100-letiya Vladivostoka, 690022, Vladivostok, Russian Federation

    D. N. Pelageev & V. Ph. Anufriev

Authors
  1. D. N. Pelageev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. V. Ph. Anufriev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to D. N. Pelageev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2290–2293, November, 2008.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pelageev, D.N., Anufriev, V.P. Condensation of hydroxy naphthazarins with aromatic aldehydes. Russ Chem Bull 57, 2335–2339 (2008). https://doi.org/10.1007/s11172-008-0332-0

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-008-0332-0

Key words

Search

Navigation