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.
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A. F. Pozharskii and A. A. Konstantinchenko, Khim. Geterotsikl. Soedin., No. 7, 964 (1979).
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).
A. F. Pozharskii, V. V. Dal'nikovskaya, S. S. Pozharskii, and A. K. Sheinkman, Khim. Geterotsikl. Soedin., No. 10, 1398 (1980).
F. Sachs, Lieb. Ann., 365, 53 (1909).
J. Burdon, W. Hollyhead, and J. Tatlow, J. Chem. Soc., No. 10, 5152 (1965).
W. A. Mosher and T. E. Banks, J. Org. Chem., 36, 1477 (1971).
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See [1] for Communication 44.
Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 6, pp. 838–842, June, 1981.
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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
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DOI: https://doi.org/10.1007/BF00503493