Skip to main content
SpringerLink
Log in

Synthesis and structure of asymmetric 2,4,6-triazidopyridines

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The reactions of 3-cyanotetrafluoropyridine and tetrachloro-3-trifluoromethylpyridine with sodium azide lead to the corresponding 2,4,6-triazido-5-cyano-3-fluoropyridine and 2,4,6-triazido-5-chloro-3-trifluoromethylpyridine. With the aid of comparative X-ray structural analysis of 2,4,6-triazido-5-cyano-3-fluoropyridine and its previously known 3-chloro-substituted derivative it was established that the geometric parameters and reactivity of the azide groups in the asymmetric 2,4,6-triazi-dopyridines depend not only on the position of these groups in the pyridine ring but also on their mutual orientation in space.

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

Fig. 1
Fig. 2
Fig. 3

Similar content being viewed by others

References

  1. Yu. M. Mikhailov, S. V. Chapyshev, and V. V. Nedel’ko, Russ. Chem. Bull, 58, 2097 (2009).

    Article  CAS  Google Scholar 

  2. S. V. Chapyshev, Synlett, 1 (2009).

  3. S. V. Chapyshev, R. Walton, J. A. Sanborn, and P. M. Lahti, J. Am. Chem. Soc., 122, 1580 (2000).

    Article  CAS  Google Scholar 

  4. E. Ya. Misochko, A. V. Akimov, and S. V. Chapyshev, J. Chem. Phys., 129, 174510 (2008).

    Article  Google Scholar 

  5. S. V. Chapyshev, D. Grote, C. Finke, and W. Sander, J. Org. Chem., 73, 7045 (2008).

    Article  CAS  Google Scholar 

  6. S. V. Chapyshev, P. Neuhaus, D. Grote, and W. Sander, J. Phys. Org. Chem., 23, 340 (2010).

    Article  CAS  Google Scholar 

  7. S. D. Moshchitskii, F. F. Zeikan’, A. F. Pavlenko, and V. P. Kukhar’, Khim. Geterotsikl. Soedin., 1492 (1979). [Chem. Heterocycl. Comp., 15, 1197 (1979)].

    Google Scholar 

  8. S. V. Chapyshev, Khim. Geterotsikl. Soedin., 1056 (2001). [Chem. Heterocycl. Comp., 37, 968 (2001)].

  9. S. V. Chapyshev, Khim. Geterotsikl. Soedin., 1650 (1993). [Chem. Heterocycl. Comp., 29, 1426 (1993)].

  10. S. V. Chapyshev and T. Ibata, Heterocycles, 36, 2185 (1993).

    Article  CAS  Google Scholar 

  11. S. V. Chapyshev, U. Bergsträsser, and M. Regitz, Khim. Geterotsikl. Soedin., 67 (1996). [Chem. Heterocycl. Comp., 32, 59 (1996)].

    Google Scholar 

  12. S. V. Chapyshev, Mendeleev Commun., 9, 164 (1999).

    Article  Google Scholar 

  13. S. V. Chapyshev and V. M. Anisimov, Khim. Geterotsikl. Soedin., 1521 (1997). [Chem. Heterocycl. Comp., 33, 1315 (1997)].

    Google Scholar 

  14. S. V. Chapyshev, Khim. Geterotsikl. Soedin., 1497 (2000). [Chem. Heterocycl. Comp., 36, 1289 (2000)].

  15. S. V. Chapyshev, Khim. Geterotsikl. Soedin., 935 (2001). [Chem. Heterocycl. Comp., 37, 861 (2001)].

  16. S. V. Chapyshev, R. Walton, and P. M. Lahti, Mendeleev Commun., 10, 187 (2000).

    Article  Google Scholar 

  17. S. V. Chapyshev, Khim. Geterotsikl. Soedin., 87 (2003). [Chem. Heterocycl. Comp., 39, 83 (2003)].

  18. S. V. Chapyshev and M. S. Platz, Mendeleev Commun., 11, 56 (2001).

    Article  Google Scholar 

  19. S. V. Chapyshev, Mendeleev Commun., 9, 166 (1999).

    Article  Google Scholar 

  20. E. Keßenich, T. M. Klapötke, J. Knizek, H. Nöth, and A. Schulz, Eur. J. Inorg. Chem., 2013 (1998).

  21. D. R. Miller, D. C. Swenson, and E. G. Gillan, J. Am. Chem. Soc., 126, 5372 (2004).

    Article  CAS  Google Scholar 

  22. C. Ye, H. Gao, J. A. Boatz, G. W. Drake, B. Twamley, and J. M. Shreeve, Angew. Chem. Int. Ed. Engl., 45, 7262 (2006).

    Article  CAS  Google Scholar 

  23. S. I. Kuzina, D. V. Korchagin, G. V. Shilov, S. V. Chapyshev, A. I. Mikhailov, and S. M. Aldoshin, Doklady Phys. Chem., 418, 7 (2008).

    Article  CAS  Google Scholar 

  24. S. I. Kuzina, D. V. Korchagin, G. V. Shilov, A. I. Mikhailov, S. V. Chapyshev, and S. M. Aldoshin, Russ. J. Phys. Chem. A, 82, 1870 (2008).

    Article  CAS  Google Scholar 

  25. S. M. Aldoshin, D. V. Korchagin, K. V. Bozhenko, G. V. Shilov, and S. V. Chapyshev, Bull. Russ. Acad. Sci.: Physics, 72, 1556 (2008).

    Article  Google Scholar 

  26. S. V. Chapyshev, V. F. Lavitskii, A. V. Akimov, E. Ya. Misochko, A. V. Shastin, D. V. Korchagin, G. V. Shilov, and S. M. Aldoshin, Russ. Chem. Bull., 57, 534 (2008).

    Article  Google Scholar 

  27. R. H. Abu-Eittah and M. K. Khedr, J. Mol. Struct.: THEOCHEM, 822, 74 (2007).

    Article  CAS  Google Scholar 

  28. A. M. Sipyagin and B. V. Kunchenko, Khim. Geterotsikl. Soedin., 657 (1994). [Chem. Heterocycl. Comp., 30, 576 (1994)].

    Google Scholar 

  29. A. M. Sipyagin and I. V. Efremov, Khim. Geterotsikl. Soedin., 1088 (1996). [Chem. Heterocycl. Comp., 32, 937 (1996)].

    Google Scholar 

  30. G. M. Sheldrick, SHELXTL v. 6.14, Structure Determination Software Suite, Bruker AXS, Madison, Wis., USA.

Download references

Author information

Authors and Affiliations

  1. Institute of Problems of Chemical Physics, Russian Academy of Sciences, 1 Acad. Semenov Ave., Chernogolovka, 142432, Moscow region, Russia

    S. V. Chapyshev, D. V. Korchagin, G. V. Shilov & S. M. Aldoshin

Authors
  1. S. V. Chapyshev
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. D. V. Korchagin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. V. Shilov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. M. Aldoshin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. V. Chapyshev.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 998–1008, July, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Chapyshev, S.V., Korchagin, D.V., Shilov, G.V. et al. Synthesis and structure of asymmetric 2,4,6-triazidopyridines. Chem Heterocycl Comp 47, 817–825 (2011). https://doi.org/10.1007/s10593-011-0841-x

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-011-0841-x

Keywords

Search

Navigation