Skip to main content
SpringerLink
Log in

Cyclization of 2-arylamino-1,4-naphthoquinones to benzo[b]phenazine-6,11-dione 5-oxides

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

Abstract

A method for the synthesis of a new group of tetracyclic diazaquinones, viz., benzo[b]-phenazine-6,11-dione 5-oxides, was developed and the pathways of their further modifications were outlined.

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. P. Krapcho, C. E. Gallagher, A. Hammach, M. Ellis, E. Menta, A. Oliva, J. Heterocycl. Chem., 1997, 34, 27.

    Article  CAS  Google Scholar 

  2. H. Nakazumi, K. Kondo, T. Kitao, Synthesis, 1982, 878.

    Google Scholar 

  3. J. A. VanAllan, G. A. Reynolds, R. E. Adel, J. Org. Chem., 1963, 28, 520.

    Article  CAS  Google Scholar 

  4. C. Baltzer, Chem. Ber., 1881, 14, 1899.

    Article  Google Scholar 

  5. T. Win, S. Yerushalmi, S. Bittner, Synthesis, 2005, 1631.

    Google Scholar 

  6. K. Fries, K. Billig, Ber. Deutsch. Chem. Ges., 1925, 58, 1128.

    Article  Google Scholar 

  7. S. P. Titova, A. K. Arinich, M. V. Gorelik, Russ. J. Org. Chem. (Engl. Transl.), 1986, 22, 1562 [Zh. Org. Khim., 1986, 22, 1562].

    CAS  Google Scholar 

  8. E. A. Bocharova, L. M. Gornostaev, N. V. Geets, Butlerov Communications, 2011, 26, No. 11, 61 [Butlerovskiye Soobshcheniya, 2011, 26, No. 11, 61].

    Google Scholar 

  9. A. L. Spek, Acta Crystallogr. Sect. D, 2009, D65, 148.

    Article  Google Scholar 

  10. F. H. Allen, Acta Crystallogr. Sect. B, 2002, B58, 380.

    Article  CAS  Google Scholar 

  11. C. F. Macrae, I. J. Bruno, J. A. Chisholm, P. R. Edgington, P. McCabe, E. Pidcock, L. Rodriguez-Monge, R. Taylor, J. van de Streek, P. A. Wood, J. Appl. Crystallogr., 2008, 41, 466.

    Article  CAS  Google Scholar 

  12. V. V. Chernyshev, Russ. Chem. Bull. (Int. Ed.), 2001, 50, 2273 [Izv. Acad. Nauk, Ser. Khim., 2001, 2171].

    Article  CAS  Google Scholar 

  13. K. D. M. Harris, E. Y. Cheung, Chem. Soc. Rev., 2004, 33, 526.

    Article  CAS  Google Scholar 

  14. W. I. F. David, K. Shankland, Acta Crystallogr. Sect. A, 2008, A64, 52.

    Article  Google Scholar 

  15. P.-E. Werner, L. Eriksson, M. Westdahl, J. Appl. Crystallogr., 1985, 18, 367.

    Article  CAS  Google Scholar 

  16. J. W. Visser, J. Appl. Crystallogr., 1969, 2, 89.

    Article  CAS  Google Scholar 

  17. V. B. Zlokazov, J. Appl. Crystallogr., 1992, 25, 69.

    Article  Google Scholar 

  18. V. B. Zlokazov, Comput. Phys. Commun., 1995, 85, 415.

    Article  CAS  Google Scholar 

  19. S. G. Zhukov, V. V. Chernyshev, E. V. Babaev, E. J. Sonneveld, H. Schenk, Z. Kristallogr., 2001, 216, 5.

    Article  CAS  Google Scholar 

  20. D. N. Laikov, Yu. A. Ustynyuk, Russ. Chem. Bull. (Int. Ed.), 2005, 54, 820 [Izv. Acad. Nauk, Ser. Khim., 2005, 804].

    Article  CAS  Google Scholar 

  21. V. B. Zlokazov, V. V. Chernyshev, J. Appl. Crystallogr., 1992, 25, 447.

    Article  Google Scholar 

  22. H. Toraya, J. Appl. Crystallogr., 1986, 19, 440.

    Article  CAS  Google Scholar 

  23. P. M. De Wolff, J. Appl. Crystallogr., 1968, 1, 108.

    Article  Google Scholar 

  24. G. M. Smith, R. L. Snyder, J. Appl. Crystallogr., 1979, 12, 60.

    Article  CAS  Google Scholar 

  25. R. A. Young, D. B. Wiles, J. Appl. Crystallogr., 1982, 15, 430.

    Article  CAS  Google Scholar 

  26. L. Kh. Vinograd, S. M. Shein, A. P. Cherepivskaya, G. V. Shalimova, Zh. Prikl. Khim. [J. Appl. Chem.], 1965, 38, 208 [CAPLUS AN 1965:66995].

    CAS  Google Scholar 

  27. C. S. Lisboa, V. G. Santos, B. G. Vaz, N. C. Lucas, M. N. Eberlin, S. J. Garden, J. Org. Chem., 2011, 76, 5264.

    Article  CAS  Google Scholar 

  28. E. Leyva, L. I. Lopez, S. E. Loredo-Carrillo, M. Rodriguez-Kessler, A. Montes-Rojas, J. Fluor. Chem., 2011, 132, 94.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. V. P. Astaf’ev Krasnoyarsk State Pedagogical University, 89 ul. A. Lebedevoi, 660049, Krasnoyarsk, Russian Federation

    L. M. Gornostaev, Yu. G. Khalyavina & T. I. Lavrikova

  2. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    G. A. Stashina & S. I. Firgang

  3. Department of Chemistry, M. V. Lomonosov Moscow State University, Build. 3, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    V. V. Chernyshev

  4. A. N. Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Korp. 4, 31 Leninsky prosp., 119071, Moscow, Russian Federation

    V. V. Chernyshev

Authors
  1. L. M. Gornostaev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yu. G. Khalyavina
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. T. I. Lavrikova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. G. A. Stashina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. S. I. Firgang
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. V. V. Chernyshev
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to L. M. Gornostaev.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0739–0743, March, 2014.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gornostaev, L.M., Khalyavina, Y.G., Lavrikova, T.I. et al. Cyclization of 2-arylamino-1,4-naphthoquinones to benzo[b]phenazine-6,11-dione 5-oxides. Russ Chem Bull 63, 739–743 (2014). https://doi.org/10.1007/s11172-014-0500-3

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-014-0500-3

Key words

Search

Navigation