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Polyfluorinated heterocyclic compounds

III. 3-Substituted tetrafluorocoumarins

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The treatment of 2-phenyl-4-carbomethoxy-6,7,8,9-tetrafluorobenz[f]oxazepin-1,3 (I), 3-benzamido-5,6,7,8-tetrafluorocoumarin (V), and α-benzamido-β-(2-hydroxy-3,4,5,6-tetrafluorophenyl)-acrylic acid (III) with a mixture of glacial acetic acid and a mineral acid gave (IV), the π-complex of 3-hydroxy-5,6,7,8-tetrafluorocoumarin (VII) and benzoic acid. Treatment of (IV) with acetic anhydride gave 3-acetoxy-5,6,7,8-tetrafluorocoumarin (VI) and benzoic acid. Treatment with diazomethane gave 3-methoxy-5,6,7,8-tetrafluorocoumarin (VIII) and methyl benzoate. IV was also obtained from an equimolar mixture of its components. A mechanism for the formation of IV from I is proposed.

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References

  1. T. D. Petrova, V. P. Mamaev, G. G. Yakobson, and N. N. Vorozhtsov Jr., ZhGS, 771, 1968.

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Authors and Affiliations

  1. Siberian Section AS USSR, Novosibirsk Institute of Organic Chemistry, USSR

    T. D. Petrova, V. P. Mamaev, G. G. Yakobson & N. N. Vorozhtsov Jr.

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  1. T. D. Petrova
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  2. V. P. Mamaev
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  3. G. G. Yakobson
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  4. N. N. Vorozhtsov Jr.
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Additional information

For part II, see [1].

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Petrova, T.D., Mamaev, V.P., Yakobson, G.G. et al. Polyfluorinated heterocyclic compounds. Chem Heterocycl Compd 4, 564–565 (1971). https://doi.org/10.1007/BF00481015

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  • DOI: https://doi.org/10.1007/BF00481015

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