Skip to main content
SpringerLink
Log in

Heterocyclic analogs of pleiadiene. 54. Synthesis, basicities, and behavior with respect to electrophilic agents of 2-fluoromethyl- and 2-difluoromethyl-perimidines. Synthesis of perimidine-6(7)-carboxylic acids

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

2-Fluoromethyl derivatives of perimidine and 1-methylperimidine were obtained by the reaction of naphthalene-1,8-diamines with bromides of fluoroacetic acids. It is demonstrated in the case of acidic deuterium exchange and trifluoro-acetylation that the decrease in the basicity in the 2-methyl-, 2-fluoromethyl-,2-difluoromethyl-, and 2-trifluoromethylperimidine series promotes electrophilic substitution in the naphthalene ring. The previously unknown 6(7)-carboxylic acids of the perimidine series were obtained by alkaline hydrolysis of the trifluoroacetyl group.

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. F. Pozharskii, V. V. Dal'nikovskaya, and T. A. Maksimova, Khim. Geterotsikl. Soedin., No. 7, 980 (1981).

    Google Scholar 

  2. A. F. Pozharskii, G. G. Yurchuk, and L. L. Gervits, Khim. Geterotsikl. Soedin., No. 3, 413 (1979).

    Google Scholar 

  3. A. F. Pozharskii and G. G. Yurchuk, Khim. Geterotsikl. Soedin., No. 3, 418 (1979).

    Google Scholar 

  4. V. I. Minkin, V. A. Bren', A. D. Garnovskii, and R. I. Nikitina, Khim. Geterotsikl. Soedin., No. 4, 552 (1972).

    Google Scholar 

  5. A. F. Pozharskii, V. N. Koroleva, O. M. Bagrova, B. A. Semavich, and V. A. Bren', Khim. Geterotsikl. Soedin., No. 1, 84 (1980).

    Google Scholar 

  6. A. F. Pozharskii, I. V. Borovlev, and I. S. Kashparov, Khim. Geterotsikl. Soedin., No. 4, 543 (1975).

    Google Scholar 

  7. A. F. Pozharskii and A. A. Konstantinchenko, Khim. Geterotsikl. Soedin., No. 7, 964 (1979).

    Google Scholar 

  8. A. F. Pozharskii, V. V. Kuz'menko, V. N. Koroleva, and G. G. Yurchuk, Khim. Geterotsikl. Soedin., No. 5, 691 (1980).

    Google Scholar 

  9. A. F. Pozharskii, I. S. Kashparov, P. J. Halls, and V. G. Zaletov, Khim. Geterotsikl. Soedin., No. 4, 543 (1971).

    Google Scholar 

  10. J. Bourdais and A. Lorre, J. Heterocycl. Chem., 12, 1111 (1975).

    Google Scholar 

  11. V. I. Minkin and V. A. Bren', Reakts. Sposob. Org. Soedin., Tartu, 4, No. 1, 113 (1967).

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Rostov State University, 344006, Rostov-on-Don

    G. G. Yurchuk & A. F. Pozharskii

Authors
  1. G. G. Yurchuk
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. A. F. Pozharskii
    View author publications

    You can also search for this author in PubMed Google Scholar

Additional information

See [1] for Communication 53

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 8, pp. 1106–1113, August, 1981.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Yurchuk, G.G., Pozharskii, A.F. Heterocyclic analogs of pleiadiene. 54. Synthesis, basicities, and behavior with respect to electrophilic agents of 2-fluoromethyl- and 2-difluoromethyl-perimidines. Synthesis of perimidine-6(7)-carboxylic acids. Chem Heterocycl Compd 17, 825–831 (1981). https://doi.org/10.1007/BF00503668

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00503668

Keywords

Search

Navigation