Skip to main content
Log in

Synthesis and investigation of some 1,4-disubstituted 2-pyrrolidinones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

A series of condensation products of 1-aryl-4-hydrazinecarbonyl-2-pyrrolidinones with acetone, 2,4-pentanedione, and aromatic aldehydes was obtained and identified by the combination of IR, mass and 1H, 13C NMR spectroscopy. The results of their structural studies by NMR spectroscopy are provided. It was ascertained that the presence of the NH group determines the existence of the mixtures of the Z/E-isomers of compounds under study. The availability of Z-isomer as a sterically favorable one was also verified by computer molecular modeling.

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. A. Kleeman and J. Engel, Pharmazeutishe Wirkstoffe, 2. Aufl., Georg Thieme Verlag, Stuttgart, 1982.

    Google Scholar 

  2. H. C. Bucha and R. W. Luckenbaugh, US Pat. 3136620; Chem. Abstr., 61, 9974 (1964).

    Google Scholar 

  3. E. Pretsch, T. Clerc, J. Seibl, and W. Simon, Tables of Spectral Data for Structure Determination of Organic Compounds, Springer-Verlag, New York, 1989.

    Google Scholar 

  4. H. O. Kalinowski, S. Berger, and S. Braun, 13 C-NMR-Spektroskopie, Georg Thieme Verlag, Stuttgart, New York, 1984.

    Google Scholar 

  5. Yu. P. Kitaev and B. I. Buzykin, Hydrazones [in Russian], Nauka, Moscow, 1974.

    Google Scholar 

  6. Yu. P. Kitaev (editor), Chemistry of hydrazones [in Russian], Nauka, Moscow, 1977.

    Google Scholar 

  7. B. V. Ioffe, M. A. Kuznetsov, and A. A. Potekhin, Chemistry of Organic Derivatives of Hydrazines [in Russian], Khimiya, Leningrad, 1979.

    Google Scholar 

  8. I. Hermecz, T. Breining, J. Sessi, and B. Podanyi, J. Heterocycl. Chem., 28, 781 (1991).

    CAS  Google Scholar 

  9. N. A. Rodios, C. A. Tsoleridis, and N. E. Alexandrou, J. Heterocycl. Chem., 25, 1161 (1988).

    Article  CAS  Google Scholar 

  10. K. M. Biswas, R. N. Dhara, D. Ganguly, H. Mallik, and S. Roy, Indian J. Chem., 25B, 1081 (1986).

    CAS  Google Scholar 

  11. D. G. Davis, J. Magn. Reson., 83, 212 (1989).

    CAS  Google Scholar 

  12. C. W. Fong and H. G. Grant, Aust. J. Chem., 34, 2307 (1981).

    Article  CAS  Google Scholar 

  13. R. M. Claramunt, C. Escoelo, and J. Elguero, ARKIVOC, 2, 1, 944 (2001).

    Google Scholar 

  14. E. C. Okafor, Spectrochim. Acta, 40A, 397 (1984).

    CAS  Google Scholar 

  15. E. Luboch and J. F. Biernat, Pol. J. Chem., 56, 1151 (1982).

    CAS  Google Scholar 

  16. G. E. Babbitt, M. P. Lynch, and J. R. Beck, Magn. Reson. Chem., 21, 90 (1990).

    Article  Google Scholar 

  17. M. Bruix, J. Mendoza, R. M. Claramunt, and J. Elguero, Magn. Reson. Chem., 23, 367 (1985).

    Article  CAS  Google Scholar 

  18. P. Ruostesuo, A. M. Hakkinen, and K. Peltola, Spectrochim. Acta, 41A, 739 (1985).

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

Published in Khimiya Geterotsiklicheskikh Soedinenii, No. 9, pp. 1336–1345, September, 2006.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Brokaite, K., Mickevicius, V. & Mikulskiene, G. Synthesis and investigation of some 1,4-disubstituted 2-pyrrolidinones. Chem Heterocycl Compd 42, 1158–1167 (2006). https://doi.org/10.1007/s10593-006-0220-1

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-006-0220-1

Keywords

Navigation