Skip to main content
Log in

Dual reactivity of diazonium salts derived from 1-amino-2-ethynyl-9,10-anthraquinones

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

Abstract

Diazotization of vicinal 1-amino-2-ethynyl-4-R-9,10-anthraquinones followed by a reaction with NaN3 gave 5-hydroxy-3-R-1H-naphtho[2,3-g]indazole-6,11-diones or 3-ethynyl-5-R-6H-anthra[1,9-cd]isoxazol-6-ones, depending on the substituents at the triply bonded C atom and in position 4 of the anthraquinone framework.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. V. M. Dembitsky, D. O. Levitsky, Nat. Prod. Commun., 2006, 1, 405.

    CAS  Google Scholar 

  2. U. Galm, M. H. Hager, S. G. Van Lanen, J. Ju, J. S. Thorson, B. Shen, Chem. Rev., 2005, 105, 739.

    Article  CAS  Google Scholar 

  3. F. Diederich, P. J. Stang, R. R. Tykwinski, Acetylene Chemistry: Chemistry, Biology and Material Science, Wiley-VCH, Weinheim, 2005, 508 pp.

    Google Scholar 

  4. T. Tuttle, E. Kraka, D. J. Cremer, J. Am. Chem. Soc., 2005, 127, 9469.

    Article  CAS  Google Scholar 

  5. J. Davies, H. Wang, T. Taylor, K. Warabi, X.-H. Huang, R. J. Andersen, Org. Lett., 2005, 7, 5233.

    Article  CAS  Google Scholar 

  6. A. G. Myers, S. B. Cohen, N. J. Tom, D. J. Madar, M. E. Fraley, J. Am. Chem. Soc., 1995, 117, 7574.

    Article  CAS  Google Scholar 

  7. S. Vasilevsky, L. Gornostaev, A. Stepanov, E. Arnold, I. Alabugin, Tetrahedron Lett., 2007, 48, 1867.

    Article  CAS  Google Scholar 

  8. A. A. Stepanov, L. M. Gornostaev, S. F. Vasilevsky, E. V. Arnold, V. I. Mamatyuk, D. S. Fadeev, B. Gold, I. V. Alabugin, J. Org. Chem., 2011, 76, 8737.

    Article  CAS  Google Scholar 

  9. M. S. Sokolova, V. A. Beresnev, O. I. Kargina, L. M. Gornostaev, Zh. Org. Khim., 2008, 44, 1654 [Russ. J. Org. Chem. (Engl. Transl.), 2008, 44].

    Google Scholar 

  10. M. S. Shvartsberg, I. D. Ivanchikova, L. G. Fedenok, Tetrahedron Lett., 1994, 35, 6749.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  12. D. N. Laikov, Chem. Phys. Lett., 1997, 281, 151.

    Article  CAS  Google Scholar 

  13. D. N. Laikov, Chem. Phys. Lett., 2005, 416, 116.

    Article  CAS  Google Scholar 

  14. J. P. Perdew, K. Burke, M. Ernzerhof, Phys. Rev. Lett., 1996, 77, 3865.

    Article  CAS  Google Scholar 

  15. D. E. Ames, D. Bull, C. Takundwa, Synthesis, 1981, 364.

    Google Scholar 

  16. V. T. Sakilidi, L. M. Gornostaev, Zh. Org. Khim., 1982, 18, 1084 [J. Org. Chem. USSR (Engl. Transl.), 1982, 18].

    CAS  Google Scholar 

  17. L. M. Gornostaev, G. F. Zeibert, G. I. Zolotareva, Khim. Geterotsikl. Soedin., 1980, 912 [Chem. Heterocycl. Compd. (Engl. Transl.), 1980, 7].

    Google Scholar 

  18. L. F. Tietze, J. Görlitzer, A. Schuffenhauer, M. Hübner, Eur. J. Org. Chem., 1999, 1075.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to S. F. Vasilevsky.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 11, pp. 2071–2078, November, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Vasilevsky, S.F., Stepanov, A.A. & Fadeev, D.S. Dual reactivity of diazonium salts derived from 1-amino-2-ethynyl-9,10-anthraquinones. Russ Chem Bull 61, 2088–2095 (2012). https://doi.org/10.1007/s11172-012-0292-2

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-012-0292-2

Key words

Navigation