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Novel rearrangement of 1,3-benzo(naphtho)dioxin-4(1)-ones under Vilsmeier-Haack reagent

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Abstract

Polyfunctional derivatives of xanthenes and benzoxanthenes in the form of organic perchlorates have been obtained by the interaction of 1,3-benzo(naphtho)dioxin-4(1)-ones with the Vilsmeier-Haack reagent at 110 °C for 5 h. The rearrangement has occurred as an electrophilic triggered recyclization due to the geminal arrangement of oxygen atoms in the six-membered ring as well as the presence of a lactone group in the structure of the starting 1,3-benzo(naphtho)dioxin-4(1)-ones.

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Authors and Affiliations

  1. Ukrainian State University of Chemical Technology, 8 Gagarina Ave, Dnipro, 49005, Ukraine

    Oleg K. Farat, Anton V. Kovtun, Svetlana A. Varenichenko & Victor I. Markov

  2. A.V. Bogatsky Physico-Chemical Institute, National Academy of Sciences of Ukraine, 86 Lyustdorfskaya Road, Odessa, 65080, Ukraine

    Aleksander V. Mazepa

Authors
  1. Oleg K. Farat
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  2. Anton V. Kovtun
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  3. Svetlana A. Varenichenko
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  4. Aleksander V. Mazepa
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  5. Victor I. Markov
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Correspondence to Oleg K. Farat.

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Farat, O.K., Kovtun, A.V., Varenichenko, S.A. et al. Novel rearrangement of 1,3-benzo(naphtho)dioxin-4(1)-ones under Vilsmeier-Haack reagent. Monatsh Chem 152, 95–101 (2021). https://doi.org/10.1007/s00706-020-02733-z

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  • DOI: https://doi.org/10.1007/s00706-020-02733-z

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