Reactions of 5-(het)aryl-1-ethyl-2(1H )-pyrazinones with terminal arylacetylenes promoted by microwave radiation

  • E. V. Verbitskiy
  • E. M. Cheprakova
  • P. A. Slepuhin
  • M. G. Pervova
  • M. A. Samorukova
  • O. N. Zabelina
  • G. L. Rusinov
  • V. N. Charushin
Article

The reaction of 5-(het)aryl-1-ethyl-2(1H)-pyrazinones with terminal arylacetylenes, leading to a mixture of two isomeric 4-aryl- and 5-aryl-substituted 2(1H)-pyridones has been investigated. The regioselectivity of this reaction has been shown on the basis of reaction mixtures study by chromato-mass spectrometry. A crystallographic investigation of the synthesized 2(1H)-pyridones and also a forecast of their potential biological activity have been carried out.

Keywords

σH-adducts arylacetylenes 1,2-dihydropyrazines ionic liquid 2(1H)-pyrazinones 2(1H)-pyridones microwave radiation 

References

  1. 1.
    J. Vekemans, C. Pollers-Wieërs, and G. Hoornaert, J. Heterocycl. Chem., 20, 919 (1983).CrossRefGoogle Scholar
  2. 2.
    G. Hoornaert, Bull. Soc. Chim. Belg., 103, 583 (1994).CrossRefGoogle Scholar
  3. 3.
    E. Van der Eycken, P. Appukkuttan, W. De Borggraeve, W. Dehaen, D. Dallinger, and C. O. Kappe, J. Org. Chem., 67, 7904 (2002).CrossRefGoogle Scholar
  4. 4.
    N. Kaval, P. Appukkuttan, and E. Van der Eycken, in: E. Van der Eycken and C. O. Kappe (editors), Topics in Heterocyclic Chemistry, Vol. 1, Springer-Verlag, Berlin-Heidelberg (2006), p.267.Google Scholar
  5. 5.
    E. V. Verbitskiy, M. V. Berezin, P. A. Slepuhin, O. N. Zabelina, G. L. Rusinov, and V. N. Charushin, Izv. Akad. Nauk, Ser. Khim., 882 (2011).Google Scholar
  6. 6.
    D. A. Filimonov, V. V. Poroikov, E. I. Karaicheva, R. K. Kazaryan, A. P. Budunova, E. M. Mikhailovskii, A. V. Rudnitskikh, L. V. Goncharenko, and Yu. V. Burov, Eksp. Klin. Farmakol., 58, No. 2, 56 (1995).Google Scholar
  7. 7.
    D. A. Filimonov and V. V. Poroikov, in: Bioactive Compound Design: Possibilities for Industrial Use, Bios Scientific Publishers, Oxford (1996), p. 47.Google Scholar
  8. 8.
    V. Poroikov and D. Filimonov, in: H.-D. Holtje and W. Sippl (editors), Rational Approaches to Drug Design, Prous Science Press, Barcelona (2001), p. 403.Google Scholar
  9. 9.
    V. V. Poroikov and D. A. Filimonov, J. Comput.-Aided Mol. Des., 16, 819 (2002).CrossRefGoogle Scholar
  10. 10.
    D. A. Filimonov and V. V. Poroikov, Ros. Khim. Zh., 50, No. 2, 66 (2006). http://www.chem.msu.su/rus/jvho/2006-2/66.pdf
  11. 11.
    L. F. Tietze and T. Eicher, Reaktionen und Synthesen im organisch-chemischen Praktikum und Forschunglaboratorium, Georg Thieme Verlag, Stuttgart, New York (1991). [Russian translation: Mir, Moscow (1999), 704 pp.]CrossRefGoogle Scholar
  12. 12.
    R. C. Clark and J. S. Reid, Acta Crystallogr., A51, 887 (1995).Google Scholar
  13. 13.
    G. M. Sheldrick, Acta Crystallogr., A64, 112 (2008).Google Scholar

Copyright information

© Springer Science+Business Media, Inc. 2011

Authors and Affiliations

  • E. V. Verbitskiy
    • 1
  • E. M. Cheprakova
    • 1
  • P. A. Slepuhin
    • 1
  • M. G. Pervova
    • 1
  • M. A. Samorukova
    • 1
  • O. N. Zabelina
    • 1
  • G. L. Rusinov
    • 1
  • V. N. Charushin
    • 1
  1. 1.I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of SciencesYekaterinburgRussia

Personalised recommendations