Skip to main content
SpringerLink
Log in

Diazabicycloalkanes with nitrogen atoms in bridgehead positions. 15. Reactions of benzo[b]-1,4-diazabicyclo[2.2.2]octene monoquaternary salt derivatives with nucleophilic reagents

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

    We’re sorry, something doesn't seem to be working properly.

    Please try refreshing the page. If that doesn't work, please contact support so we can address the problem.

Abstract

Monoquaternary salt derivatives of benzo[b]-1,4-diazabicyclo[2.2.2]octene react with piperidine and sodium methoxide or 4-tert-butylthiophenoxide to give primarily N,N-disubstituted tetrahydroquinoxalines. Rate constants have been measured for these bimolecular reactions. Based on their levels of reactivity, these quaternary salts behave as typical alkylating agents.

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

Literature Cited

  1. G. V. Shishkin and V. N. Sil'nikov, Khim. Geterotsikl. Soedin., No. 12, 1658 (1986).

    Google Scholar 

  2. G. Cerichelli, G. Illuminati, and C. Lillocci, J. Org. Chem., 45, 3952 (1980).

    Google Scholar 

  3. G. Cospito, G. Illuminati, C. Lillocci, and H. Petride, J. Org. Chem., 46, 2944 (1981).

    Google Scholar 

  4. A. A. Gall' and G. V. Shishkin, Khim. Geterotsikl. Soedin., No. 6, 831 (1980).

    Google Scholar 

  5. G. W. H. Cheeseman and R. F. Cookson, The Chemistry of Heterocyclic Compounds, Wiley, New York (1979), Vol. 35, p. 261.

    Google Scholar 

  6. T. S. Manoharan, K. M. Madyastha, B. B. Singh, S. F. Bhafnagar, and U. Weiss, Synthesis, No. 10, 261 (1983).

    Google Scholar 

  7. O. V. Sverdlova, Electronic Spectra in Organic Chemistry [in Russian], Khimiya, Leningrad (1973), p. 195.

    Google Scholar 

  8. G. M. Panchenkov and V. P. Lebedev, Chemical Kinetics and Catalysis [in Russian], Izd. Mask. Gos. Univ., Moscow (1961), p. 17, 35.

    Google Scholar 

  9. M. Charton, Progress in Physical Organic Chemistry, R. W. Taft (ed.), Wiley, New York (1981), Vol. 13, p. 119.

    Google Scholar 

  10. N. B. Chapman, J. Biggs, and A. Finch, J. Chem. Soc., B, No. 1, 55 (1971).

    Google Scholar 

  11. R. W. Hoffmann, Mechanisms of Chemical Reactions [Russian translation], Khimiya, Moscow (1979), p. 52.

    Google Scholar 

  12. V. A. Pal'm and T. L. Tenno, Tables of Rate Constants and Equilibrium Constants for Heterolytic Organic Reactions [in Russian], VINITI, Moscow (1977), Vol. 2, Part 2, p. 186.

    Google Scholar 

  13. G. V. Shishkin and G. A. Zloba, USSR Patent No. 749835; Byull. Izobr., No. 27, p. 101 (1980).

Download references

Author information

Authors and Affiliations

  1. Novosibirsk Institute of Bioorganic Chemistry, Siberian Branch, Academy of Sciences of the USSR, 630090, Novosibirsk

    N. P. Luk'yanchuk, N. I. Sagalaeva, V. K. Soboleva & G. V. Shishkin

Authors
  1. N. P. Luk'yanchuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. N. I. Sagalaeva
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. V. K. Soboleva
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. G. V. Shishkin
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

For communication 14, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 966–972, July, 1987.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Luk'yanchuk, N.P., Sagalaeva, N.I., Soboleva, V.K. et al. Diazabicycloalkanes with nitrogen atoms in bridgehead positions. 15. Reactions of benzo[b]-1,4-diazabicyclo[2.2.2]octene monoquaternary salt derivatives with nucleophilic reagents. Chem Heterocycl Compd 23, 792–798 (1987). https://doi.org/10.1007/BF00475654

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00475654

Keywords

Search

Navigation