Skip to main content
Log in

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

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

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.

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.

Fig. 1

Similar content being viewed by others

References

  1. J. Vekemans, C. Pollers-Wieërs, and G. Hoornaert, J. Heterocycl. Chem., 20, 919 (1983).

    Article  CAS  Google Scholar 

  2. G. Hoornaert, Bull. Soc. Chim. Belg., 103, 583 (1994).

    Article  CAS  Google Scholar 

  3. E. Van der Eycken, P. Appukkuttan, W. De Borggraeve, W. Dehaen, D. Dallinger, and C. O. Kappe, J. Org. Chem., 67, 7904 (2002).

    Article  Google Scholar 

  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. 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).

  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).

    CAS  Google Scholar 

  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. 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. V. V. Poroikov and D. A. Filimonov, J. Comput.-Aided Mol. Des., 16, 819 (2002).

    Article  CAS  Google Scholar 

  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. 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.]

    Book  Google Scholar 

  12. R. C. Clark and J. S. Reid, Acta Crystallogr., A51, 887 (1995).

    CAS  Google Scholar 

  13. G. M. Sheldrick, Acta Crystallogr., A64, 112 (2008).

    CAS  Google Scholar 

Download references

The work was carried out with the financial support for Programs of the Ural Branch Russian Academy of Sciences 09-I-3-2004, 09-P-3-1015, 09-T-3-1022, Goscontract No. 02.740.11.0260, and also grants from the Russian Fund for Fundamental Investigations (RFFI) 10-03-96078-r_ural_a and VNSh-65261.2010.3.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to E. V. Verbitskiy.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 860–870, June, 2011.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Verbitskiy, E.V., Cheprakova, E.M., Slepuhin, P.A. et al. Reactions of 5-(het)aryl-1-ethyl-2(1H )-pyrazinones with terminal arylacetylenes promoted by microwave radiation. Chem Heterocycl Comp 47, 710–718 (2011). https://doi.org/10.1007/s10593-011-0824-y

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-011-0824-y

Keywords

Navigation