Skip to main content
SpringerLink
Log in

Heterocyclic analogs of 5,12-naphthacene-quinone. 3. Synthesis of 4,11-diaminonaphtho-[2,3-f]indole-5,10-dione and certain of its derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

Nucleophilic substitution of methoxy groups in 4,11-dimethoxynaphtho[2,3-f]indole-5,10-dione by the action of primary and secondary alkylamines, or arylamines leads to the formation of N-alkyl or N-aryl derivatives of 4,11-diaminonaphtho[2,3-f]indole-5,10-dione respectively. 4,11-Diamino-1H-naphtho-[2,3-f]indole-5,10-dione is obtained by the dealkylation of 4,11-bis[(1-phenylethyl)amino]-1Hnaphtho[ 2,3-f]indole-5,10-dione in the presence of a Lewis acid (BBr3).

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. A. E. Shchekotikhin, Yu. N. Luzikov, O. S. Anisimova, V. N. Buyanov, and M. N. Preobrazhenskaya, Khim. Geterotsikl. Soedin., 691 (2006).

  2. A. E. Shchekotikhin, V. N. Buyanov, K. F. Turchin, E. P. Baberkina, G. V. Avramenko, and N. N. Suvorov, Khim. Geterotsikl. Soedin., 1050 (1996).

  3. A. E. Shchekotikhin, E. P. Baberkina, V. N. Buyanov, K. F. Turchin, and N. N. Suvorov, Khim. Geterotsikl. Soedin., 1030 (2001).

  4. A. E. Shchekotikhin, V. N. Buyanov, and M. N. Preobrazhenskaya, Bioorg. Med. Chem., 32, 3923 (2004).

    Article  CAS  Google Scholar 

  5. M. Smith in: March’s Advanced Organic Chemistry: Reactions, Mechanisms and Structure, 5th Edit., John Wiley & Sons (2001), p. 860.

  6. M. V. Gorelik, Chemistry of Anthraquinones and Their Derivatives [in Russian], Khimiya, Moscow (1983), p. 200.

    Google Scholar 

  7. G. Gehrke and L. Nussler, Brit. Pat. 807241 (1960); Chem. Abstr., 54, 1873 (1960).

    Google Scholar 

  8. K. Naiki, E. Cho, and S. Tsuruoka, J. Synth. Org. Chem., 17, 705 (1959).

    CAS  Google Scholar 

  9. A. P. Krapcho, K. J. Shaw, J. J. Landi, and D. J. Phinney, J. Org. Chem., 49, 5253 (1984).

    Article  CAS  Google Scholar 

  10. V. Ya. Fain, in: Electronic Absorption Spectra and the Structure of Anthraquinones, Vol. 1, 9,10-Anthraquinone and Its Monosubstituted Derivatives [in Russian], Sputnik (2003), p. 149.

  11. Bayer AG, Neth. Pat. Appl., 6610880 (1967); Chem. Abstr., 67, 65423 (1967).

  12. V. Ya. Fain, in: Electronic Absorption Spectra and the Structure of Anthraquinones, Vol. 2, Disubstituted 9, 10-Anthraquinones [in Russian], Sputnik (2003), p. 84.

  13. B. I. Stepanov, Introduction to the Chemistry and Technology of Organic Dyestuffs, 3rd Ed. [in Russian], Khimiya, Moscow (1983), p. 200.

    Google Scholar 

  14. M. J. Kamlet, J. L. Abboud, and R. W. Taft, in: R. W. Taft (editor), Progress in Physical Organic Chemistry, Vol. 13, John Wiley & Sons (1981), p. 485.

Download references

Author information

Authors and Affiliations

  1. G. F. Gauze Institute of New Antibiotics, the Russian Academy of Medical Science Moscow, 119021, Russia

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

  2. Russian D. I. Mendeleev University of Chemical Technology, Moscow, 125190

    V. N. Buyanov

Authors
  1. A. E. Shchekotikhin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu. N. Luzikov
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. N. Buyanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. M. N. Preobrazhenskaya
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

__________

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 854–861, June, 2006.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shchekotikhin, A.E., Luzikov, Y.N., Buyanov, V.N. et al. Heterocyclic analogs of 5,12-naphthacene-quinone. 3. Synthesis of 4,11-diaminonaphtho-[2,3-f]indole-5,10-dione and certain of its derivatives. Chem Heterocycl Compd 42, 746–752 (2006). https://doi.org/10.1007/s10593-006-0156-5

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-006-0156-5

Keywords

Search

Navigation