Skip to main content
SpringerLink
Log in

Diazabicycloalkanes with nitrogen atoms in bridgehead positions.

18. Intramolecular cyclization of 1-(β-haloethyl)-1,2,3,4-tetrahydroquinoxalinium salts in acidic media

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

1-Methyl-1-(β-haloethyl)-1,2,3,4-tetrahydroquinoxalinium salts were synthesized and the dependence of the hydrolysis and cyclization rate constants on the acidity of the medium and presence of halide was found. It was determined that the monocations of tetrahydroquinoxalines participate in the formation of the benzo[b]-1,4-diazabicyclo[2.2.2]octene system, since blocking the free electron pair of the tertiary nitrogen atom with a methyl substituent significantly accelerates the cyclization and suppresses the hydrolytic side reaction.

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. A. A. Gall', S. O. Doronina, G. V. Shishkin, A. A. Voityuk, and A. A. Bliznyuk, Khim. Geterotsikl. Soedin., No. 3, 366 (1989).

    Google Scholar 

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

    Google Scholar 

  3. U. Ross, Biological Alkylating Agents [in Russian], Meditsina, Moscow (1964).

    Google Scholar 

  4. B. Beksha and I. Degutis, Zh. Org. Khim., 1, 1842 (1965).

    Google Scholar 

  5. M. G. Ahmed, R. W. Alder, G. H. James, M. L. Sinnott, and M. C. Whiting, J. Chem. Soc., Chem. Commun., No. 23, 1533 (1968).

    Google Scholar 

  6. N. P. Luk'yanchuk, N. I. Sagalaeva, V. K. Soboleva, and G. V. Shishkin, Khim. Geterotsikl. Soedin., No. 7, 966 (1987).

    Google Scholar 

  7. J. C. Cavagnol and W. J. Gordon, J. Am. Chem. Soc., 72, 3752 (1950).

    Google Scholar 

  8. G. P. Tuszynski, M. Frederick, and R. G. Kallen, J. Am. Chem. Soc., 97, 7359.

  9. J. S. Morley, J. Chem. Soc., 4002 (1952).

  10. L. S. Yaguzhinskii and A. A. Selishcheva, Zh. Org. Khim., 42, 2087 (1972).

    Google Scholar 

  11. L. B. Mrachkovskaya and L. N. Yakhontov, Khim. Geterotsikl. Soedin., No. 6, 845 (1976).

    Google Scholar 

  12. S. M. McElvain and L. W. Bannister, J. Am. Chem. Soc., 76, 1126 (1954).

    Google Scholar 

  13. V. A. Pal'ma (ed.), Tables of Rate Constants and Equilibria of Heterocyclic Organic Reactions, Vol. 2, Suppl. 2 [in Russian], Izd. VINITI, Moscow (1977), p. 132, 140.

    Google Scholar 

  14. A. Jermakova, P. Valko, and S. Vajda, Appl. Catal., 2, 139 (1982).

    Google Scholar 

  15. H.-J. Schumacher and S. Lenker, Berichte, 61, 1671 (1928).

    Google Scholar 

Download references

Author information

Authors and Affiliations

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

    S. O. Doronina, A. A. Gall' & G. V. Shishkin

Authors
  1. S. O. Doronina
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. A. Gall'
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. G. V. Shishkin
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

For Communication 17, see [1].

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 372–378, March, 1989.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Doronina, S.O., Gall', A.A. & Shishkin, G.V. Diazabicycloalkanes with nitrogen atoms in bridgehead positions.. Chem Heterocycl Compd 25, 311–316 (1989). https://doi.org/10.1007/BF00472392

Download citation

  • Received:

  • Revised:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00472392

Keywords

Search

Navigation