Skip to main content
SpringerLink
Log in

Synthesis of 5-substituted 8,8-dimethyl-8,9-dihydro-3H,7H-[1,2]oxazino[5,4,3-de]quinolin-3-ones

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

The reaction of 2-substituted 7,7-dimethyl-5-oxo-5,6,7,8-tetrahydroquinoline-4-carboxylic acids with hydroxylamine results in the formation of 5-substituted 8,8-dimethyl-8,9-dihydro-3H,7H-[1,2]ox-azino[5,4,3-de]quinolin-3-ones. The structure of the 5-phenyl derivative has been established by X-ray structural analysis. A possible mechanism of the reaction has been proposed on the basis of nonempirical quantum-chemical calculations.

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

Fig. 1

Similar content being viewed by others

References

  1. A. Maeder, Helv. Chim. Acta, 29, 120 (1946).

    Article  CAS  Google Scholar 

  2. M. Masaki, H. Matsucubo, K. Masuzawa, Y. Chigira, and M. Ohta, J. Heterocycl. Chem., 2, 376 (1965).

    Article  CAS  Google Scholar 

  3. B. Hardegger and S. Shatzmiller, Helv. Chim. Acta, 59, 2499 (1976).

    Article  CAS  Google Scholar 

  4. C. P. Sakthidharan and N. Sampathkumar, Heterocycl. Lett., 1, 43 (2011).

    Google Scholar 

  5. D. A. Rudenko, S. N. Shurov, M. I. Kodess, M. A. Ezhikova, and A. N. Vasyanin, Zh. Org. Khim., 48, 803 (2012).

    Google Scholar 

  6. A. A. Granovsky, Firefly version 7.1.G, http://classic.chem.msu.su/gran/firefly/index.html (application date: 07.02.2012).

  7. CrysAlis Pro, Version 171.33.66, Oxford Diffraction Ltd.

  8. G. M. Sheldrick, Acta Crystallogr., Sect. A: Found. Crystallogr., A64, 112 (2008).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Perm State National Research University, 15 Bukireva St., Perm, 614990, Russia

    D. A. Rudenko, S. N. Shurov, M. I. Vakhrin & Yu. A. Shchurov

  2. Institute of Organic Synthesis, Ural Branch, Russian Academy of Science, 22 S. Kovalevskoi St., Yekaterinburg, 620041, Russia

    P. A. Slepukhin

  3. Institute of Technical Chemistry, Ural Branch, Russian Academy of Science, 3 Akademika Koroleva St., Perm, 614013, Russia

    V. I. Karmanov

Authors
  1. D. A. Rudenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. P. A. Slepukhin
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. I. Karmanov
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. S. N. Shurov
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. I. Vakhrin
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Yu. A. Shchurov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. N. Shurov.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 10, 1651-1656, October, 2012.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Rudenko, D.A., Slepukhin, P.A., Karmanov, V.I. et al. Synthesis of 5-substituted 8,8-dimethyl-8,9-dihydro-3H,7H-[1,2]oxazino[5,4,3-de]quinolin-3-ones. Chem Heterocycl Comp 48, 1539–1544 (2013). https://doi.org/10.1007/s10593-013-1170-z

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-013-1170-z

Keywords

Search

Navigation