Skip to main content
Log in

α-Nitro chalcones: Structure and reaction with pyrrole

  • Published:
Russian Journal of General Chemistry Aims and scope Submit manuscript

Abstract

According to the 1H NMR, IR, and electronic absorption spectra and X-ray diffraction data, 2-aryl-1-benzoyl-1-nitroethenes have E configuration with predominant s-cis conformation, where the nitro group lies in the plane of the double carbon-carbon bond, while the carbonyl group deviates from that plane. Reactions of 2-aryl-1-benzoyl-1-nitroethenes with pyrrole and N-methylpyrrole gave the corresponding alkylation products at the C2 atom in the heteroring.

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. Yanovskaya, L.A., Kryshtal’, G.V., and Kul’ganek, V.V., Usp. Khim., 1984, vol. 53, no. 8, p. 1280.

    CAS  Google Scholar 

  2. Orlov, V.D., Kolosov, M.A., Kotlyar, V.N., Marrugo Gonzalez, A.Kh., Sidorenko, D.Yu., Pushkarev, A.P., and Baraban, A.Yu., Sbornik nauchnykh trudov Vserossiiskoi nauchno-prakticheskoi konferentsii “Korshunovskie chteniya” (Collection of Scientific Papers Presented at the All-Russian Scientific and Practical Conf. “Korshunov’s Readings”), Tol’yatti, 2008, p. 11.

  3. Shikhaliev, Kh.E., Falaleev, A.V., and Kryl’skii, D.V., Izbrannye metody sinteza i modifikatsii geterotsiklov (Selected Methods of Synthesis and Modification of Heterocycles), Kartsev, V.G., Ed., Moscow: IBS, 2003, vol. 1, p. 450.

    Google Scholar 

  4. Desenko, S.M., Chebanov, V.A., Kolos, N.N., and Orlov, V.D., Izbrannye metody sinteza i modifikatsii geterotsiklov (Selected Methods of Synthesis and Modification of Heterocycles), Kartsev, V.G., Ed., Moscow: IBS, 2003, vol. 1, p. 140.

    Google Scholar 

  5. Desenko, S.M. and Orlov, V.D., Azageterotsikly na osnove aromaticheskikh nepredel’nykh ketonov (Aza Heterocycles Based on Aromatic Unsaturated Ketones), Khar’kov: Folio, 1998.

    Google Scholar 

  6. Fel’gendler, A.V., Aboskalova, N.I., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2000, vol. 70, no. 7, p. 1087.

    Google Scholar 

  7. Bakhareva, S.V., Aboskalova, N.I., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2001, vol. 71, no. 9, p. 1493.

    Article  CAS  Google Scholar 

  8. Aboskalova, N.I., Berestovitskaya, V.M., Bakhareva, S.V., and Fel’gendler, A.V., Khim. Geterotsikl. Soedin., 2002, no. 10, p. 1462.

  9. Berestovitskaya, V.M., Aboskalova, N.I., Ishmaeva, E.A., Bakhareva, S.V., Berkova, G.A., Vereshchagina, Ya.A., Fel’gendler, A.V., and Fattakhova, G.R., Russ. J. Gen. Chem., 2001, vol. 71, no. 12, p. 1942.

    Article  CAS  Google Scholar 

  10. Remennikov, G.A., Khim. Geterotsikl. Soedin., 1997, no. 12, p. 1587.

  11. Paperno, T.Ya., Perekalin, V.V., and Sopova, A.S., Zh. Prikl. Spektrosk., 1973, vol. 19, no. 4, p. 649.

    CAS  Google Scholar 

  12. Savin, V.I. and Kitaev, Yu.P., Zh. Org. Khim., 1973, vol. 9, no. 6, p. 1101.

    CAS  Google Scholar 

  13. Bellamy, L.J., Advances in Infra-red Group Frequencies, London: Methuen, 1966. Translated under the title Novye dannye po IK spektram slozhnykh molekul, Moscow: Mir, 1971, p. 172.

    Google Scholar 

  14. He, L., Srikanth, G.S.C., and Castle, S.L., J. Org. Chem., 2005, vol. 70, no. 20, p. 8140.

    Article  CAS  Google Scholar 

  15. Aboskalova, N.I., Smirnova, N.N., Kataeva, O.N., Baichurin, R.I., Fel’gendler, A.V., Berkova, G.A., and Berestovitskaya, V.M., Russ. J. Gen. Chem., 2008, vol. 78, no. 9, p. 1711.

    Article  CAS  Google Scholar 

  16. Andrianov, V.G., Struchkov, Yu.T., and Babievsky, K.K., Cryst. Struct. Commun., 1982, vol. 11, p. 31.

    CAS  Google Scholar 

  17. Aboskalova, N.I., Berestovitskaya, V.M., Berkova, G.A., and Fel’gendler, A.V., Russ. J. Org. Chem., 1999, vol. 35, no. 1, p. 151.

    CAS  Google Scholar 

  18. Sheldrick, G.M., SHELXTL Ver.5.0. Software Reference Manual, Siemens Industrial Automation: Madison WI, 1995.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to V. M. Berestovitskaya.

Additional information

Original Russian Text © V.M. Berestovitskaya, R.I. Baichurin, N.I. Aboskalova, K.A. Lysenko, G.A. Berkova, A.V. Fel’gendler, 2009, published in Zhurnal Obshchei Khimii, 2009, Vol. 79, No. 10, pp. 1697–1702.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Berestovitskaya, V.M., Baichurin, R.I., Aboskalova, N.I. et al. α-Nitro chalcones: Structure and reaction with pyrrole. Russ J Gen Chem 79, 2191–2196 (2009). https://doi.org/10.1134/S1070363209100181

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070363209100181

Keywords

Navigation