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Chemistry of Heterocyclic Compounds

, Volume 55, Issue 1, pp 38–46 | Cite as

A facile approach for the synthesis of novel xanthene derivatives with Vilsmeier–Haack reagent

  • Oleg K. FaratEmail author
  • Ivan V. Ananyev
  • Svetlana A. Varenichenko
  • Ekaterina V. Zaliznaya
  • Victor I. Markov
Article
  • 27 Downloads

A series of new derivatives of formylxanthenes have been synthesized via the reaction of substituted 1,3-benzoxazines with Vilsmeier–Haack reagent. It has been shown that 1,3-benzoxazines unsubstituted in the aromatic part and 6-bromo-1,3-benzoxazines are rearranged into xanthene derivatives under heating at 80°C for 1.5 h. Substitution at the C-8 position of 1,3-benzoxazines, especially with electronegative groups significantly inhibits the reaction. So, the presence of iodine atoms at the C-6 and C-8 positions leads to increase in reaction time up to 8 h, the presence of bromine atom in the C-8 position requires heating up to 100°C for 11 h.

Keywords

Vilsmeier–Haack reagent xanthene derivatives crystal structure rearrangement 

Notes

I. V. Ananyev is thankful to the Russian Foundation for Basic Research (project № 18-33-20075) for the financial support of X-ray diffraction studies and DFT calculations.

Authors are grateful to Dr. N. E. Borisova for NMR studies. The NMR measurements were supported by the Laboratory of Magnetic Tomography and Spectroscopy of Chemical Department of the Moscow State University.

Supplementary material

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Copyright information

© Springer Science+Business Media, LLC, part of Springer Nature 2019

Authors and Affiliations

  • Oleg K. Farat
    • 1
    Email author
  • Ivan V. Ananyev
    • 2
    • 3
  • Svetlana A. Varenichenko
    • 4
  • Ekaterina V. Zaliznaya
    • 4
  • Victor I. Markov
    • 4
  1. 1.Chemistry DepartmentM. V. Lomonosov Moscow State UniversityMoscowRussia
  2. 2.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussia
  3. 3.Plekhanov Russian University of EconomicsMoscowRussia
  4. 4.Ukrainian State University of Chemical TechnologyDniproUkraine

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