Skip to main content
Log in

Heterocyclic analogs of pleiadiene. 45. Recyclization of 1-methylperimidine under the influence of fluorobenzoyl chlorides. Unexpected formation of tetrafluoro-phthaloperinone in the case of pentafluorobenzoyl chloride

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The action of isomeric fluorobenzoyl chlorides on 1-methylperimidine in the presence of triethylamine gave N-methyl-N-formyl-N-fluorobenzoyl-1,8-naphthalenediamines, which on treatment with a solution of alkali are converted smoothly to 1-methyl-2-fluorophenylperimidines. Pentafluorobenzoyl chloride does not undergo this reaction but under absolute conditions at high temperatures forms 11,12,13,14-tetra-fluorophthaloperin-10-one.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

Literature cited

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

    Google Scholar 

  2. A. F. Pozharskii, V. V. Dal'nikovskaya, V. I. Sokolov, A. A. Konstantinchenko, 0. V. Yarikova, and L. L. Popova, Khim. Geterotsikl. Soedin., No. 8, 1125 (1978).

    Google Scholar 

  3. A. F. Pozharskii, V. V. Dal'nikovskaya, S. S. Pozharskii, and A. K. Sheinkman, Khim. Geterotsikl. Soedin., No. 10, 1398 (1980).

    Google Scholar 

  4. F. Sachs, Lieb. Ann., 365, 53 (1909).

    Google Scholar 

  5. J. Burdon, W. Hollyhead, and J. Tatlow, J. Chem. Soc., No. 10, 5152 (1965).

    Google Scholar 

  6. W. A. Mosher and T. E. Banks, J. Org. Chem., 36, 1477 (1971).

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Additional information

See [1] for Communication 44.

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 838–842, June, 1981.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Pozharskii, A.F., Yurchuk, G.G. Heterocyclic analogs of pleiadiene. 45. Recyclization of 1-methylperimidine under the influence of fluorobenzoyl chlorides. Unexpected formation of tetrafluoro-phthaloperinone in the case of pentafluorobenzoyl chloride. Chem Heterocycl Compd 17, 627–631 (1981). https://doi.org/10.1007/BF00503493

Download citation

  • Received:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF00503493

Keywords

Navigation