Skip to main content
SpringerLink
Log in

Methyl 3-aroyl-4-oxo-1,4-dihydroquinoline-2-carboxylates: synthesis and molecular and crystal structures

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

Abstract

Thermal decarbonylation of methyl 1-aryl-3-(het)aroyl-4,5-dioxo-4,5-dihydro-1H-pyrrole-2-carboxylates afforded 8-substituted methyl 3-(het)aroyl-4-oxo-1,4-dihydroquinoline-2-carboxylates. X-ray diffraction studies revealed no hydrogen bonds in the crystals of the compounds obtained. According to spectral data, hydrogen bonding is possible in concentrated solutions of 8-substituted methyl 4-oxo-1,4-dihydroquinoline-2-carboxylates.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. L. Vasrar-Debreczy, J. Hermecz, Z. Meszaros, P. Dvortsok, G. Toth, J. Chem. Soc., Perkin Trans. 1, 1980, 227.

    Google Scholar 

  2. A. N. Maslivets, O. P. Krasnykh, L. I. Smirnova, Yu. S. Andreichikov, Zh. Org. Khim., 1989, 25, 1045 [J. Org. Chem. USSR (Engl. Transl.), 1989, 25, 941].

    CAS  Google Scholar 

  3. C. Wentrup, V. V. Ramana Rao, W. Frank, B. E. Fulloon, D. W. J. Moloney, T. Mosandl, J. Org. Chem., 1999, 64, 3608.

    Article  CAS  Google Scholar 

  4. Quinolone Antimicrobial Agents, Eds D. C. Hooper, E. Rubinstein, Washington, ASM Press, 2003.

    Google Scholar 

  5. Yu. S. Andreichikov, A. N. Maslivets, L. I. Smirnova, O. P. Krasnykh, A. P. Kozlov, L. A. Perevozchikov, Zh. Org. Khim., 1987, 23, 1534 [J. Org. Chem. USSR (Engl. Transl.), 1987, 23].

    CAS  Google Scholar 

  6. Comprehensive Organic Chemistry, Ed. P. G. Sammes, Pergamon, Oxford, 1979, Vol. 4.

    Google Scholar 

  7. M. J. Mphahlele, A. M. El-Nahas, J. Mol. Struct., 2004, 688, 129.

    Article  CAS  Google Scholar 

  8. F. H. Alen, O. Kennard, D. G. Watson, L. Brammer, A. G. Orpin, R. Taylor, J. Chem. Soc., Perkin Trans. 2, 1987, 1.

    Google Scholar 

  9. CrysAlis RED, Version 1.171.28cycle4 beta (Release 11-11-2005 CrysAlis171.NET), Oxford Diffraction Ltd., 2005.

  10. G. M. Sheldrick, SHELXS97. Program for the Solution of Crystal Structure, University of Göttingen, Göttingen (Germany), 1997.

    Google Scholar 

  11. G. M. Sheldrick, SHELXL97. Program for the Refinement of Crystal Structure, University of Göttingen, Göttingen (Germany), 1997.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Perm National Research Polytechnic University, 29 Komsomol’skii prosp., 614990, Perm, Russian Federation

    A. A. Boteva, O. P. Krasnykh & I. V. Fefilova

  2. Perm State Pharmaceutical Academy, 2 ul. Polevaya, 614990, Perm, Russian Federation

    E. B. Babushkina

  3. I. Ya. Postovskii Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoi, 620990, Ekaterinburg, Russian Federation

    P. A. Slepukhin

Authors
  1. A. A. Boteva
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. O. P. Krasnykh
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. I. V. Fefilova
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. E. B. Babushkina
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. P. A. Slepukhin
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to A. A. Boteva.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 3, pp. 0731–0738, March, 2014.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Boteva, A.A., Krasnykh, O.P., Fefilova, I.V. et al. Methyl 3-aroyl-4-oxo-1,4-dihydroquinoline-2-carboxylates: synthesis and molecular and crystal structures. Russ Chem Bull 63, 731–738 (2014). https://doi.org/10.1007/s11172-014-0499-5

Download citation

  • Received:

  • Revised:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11172-014-0499-5

Key words

Search

Navigation