Skip to main content
Log in

Direct C-C-coupling of ferrocenyl- and cymantrenyllithium with 5-(het)aryl-1,2,5-oxadiazolo[3,4-b]pyrazines

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

Abstract

A direct C-C-coupling of ferrocenyl- and cymantrenyllithium with 5-(het)aryl-1,2,5- oxadiazolo[3,4-b]pyrazines was accomplished. Main characteristics of the S N H-reaction products were obtained, as well as crystallographic data on the spatial structure of oxadiazolopyrazinylferrocenes and -cymantrenes synthesized.

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. I. A. Utepova, O. N. Chupakhin, V. N. Charushin, Heterocycles, 2008, 76, 39.

    Article  CAS  Google Scholar 

  2. O. N. Chupakhin, I. A. Utepova, I. S. Kovalev, V. L. Rusinov, Z. A. Starikova, Eur. J. Org. Chem., 2007, 5, 857.

    Article  Google Scholar 

  3. I. A. Utepova, A. A. Musikhina, O. N. Chupakhin, P. A. Slepukhin, Organometallics, 2011, 30, 3047.

    Article  CAS  Google Scholar 

  4. Ferrocenes: Homogeneous Catalysis — Organic Synthesis — Materials Science, Eds A. Togni, T. Hayashi, VCH, Weinheim, 1995.

    Google Scholar 

  5. C. Sporer, H. Heise, K. Wurst, D. Ruiz-Molina, H. Kopacka, P. Jaitner, F. Köhler, J. J. Novoa, J. Veciana, Chem. Eur. J., 2004, 10, 1355.

    Article  CAS  Google Scholar 

  6. R. C. J. Atkinson, V. C. Gibson, N. J. Long, Chem. Soc. Rev., 2004, 33, 313.

    Article  CAS  Google Scholar 

  7. A. A. Simenel, G. A. Dokuchaeva, L. V. Snegur, A. N. Rodionov, M. M. Ilyin, S. I. Zykova, L. A. Ostrovskaya, N. V. Bluchterova, M. M. Fomina, V. A. Rikova, Appl. Organomet. Chem., 2011, 25, 70.

    Article  CAS  Google Scholar 

  8. K. Splith, W. Hu, U. Schatzschneider, R. Gust, I. Ott, L. A. Onambele, A. Proko, I. Neundorf, Bioconjugate Chem., 2010, 21, 1288.

    Article  CAS  Google Scholar 

  9. A. G. Ginzburg, Usp. Khim., 2009, 78, 211 [Russ. Chem. Rev. (Engl. Transl.), 2009, 78].

    Article  Google Scholar 

  10. E. V. Verbitskii, Yu. A. Kvashnin, P. A. Slepukhin, A. V. Kuchin, G. L. Rusinov, O. N. Chupakhin, V. N. Charushin, Izv. Akad. Nauk, Ser. Khim., 2011, 898 [Russ. Chem. Bull., Int. Ed., 2011, 60, 919].

    Google Scholar 

  11. O. N. Chupakhin, V. N. Charushin, H. van der Plas, Nucleophilic Aromatic Substitution of Hydrogen, Academic Press, New York-San Diego, 1994, 367 pp.

    Google Scholar 

  12. B. J. Drouin, T. G. Lavaty, P. A. Cassak, S. G. Kukolich, J. Chem. Phys., 1997, 107, 6541.

    Article  CAS  Google Scholar 

  13. A. V. Eremeev, V. G. Andrianov, I. P. Piskunova, Khim. Geterotsikl. Soedin., 1978, 613 [Chem. Heterocycl. Compd. (Engl. Transl.), 1978, 14, 500].

    Google Scholar 

  14. G. M. Sheldrick, Acta Crystallorg., Sect. A, 2008, 64, 112.

    Article  Google Scholar 

  15. R. C. Clark, J. S. Reid, Acta Crystallorg., Sect. A, 1995, 51, 887.

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to I. A. Utepova.

Additional information

Dedicated to Academician of the Russian Academy of Sciences R. Z. Sagdeev on the occasion of his 70th birthday.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 12, pp. 2482–2486, December, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Utepova, I.A., Musikhina, A.A., Kvashnin, Y.A. et al. Direct C-C-coupling of ferrocenyl- and cymantrenyllithium with 5-(het)aryl-1,2,5-oxadiazolo[3,4-b]pyrazines. Russ Chem Bull 60, 2531–2535 (2011). https://doi.org/10.1007/s11172-011-0389-z

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-011-0389-z

Key words

Navigation