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Chemistry of Heterocyclic Compounds

, Volume 50, Issue 8, pp 1081–1089 | Cite as

Tautomeric Forms of 3-Formyl- 4-Hydroxycoumarin Arylhydrazones

  • V. S. Lebedev
  • B. G. Milevskii
  • N. P. Solov’eva
  • T. A. Chibisova
  • O. N. Kazheva
  • O. A. Dyachenko
  • G. G. Alexandrov
  • V. F. TravenEmail author
Article

Tautomeric forms of 3-formyl-4-hydroxycoumarin arylhydrazones were studied by 1H and 13C NMR spectroscopy, as well as X-ray structural analysis. These compounds were shown to exist primarily in the 4-hydroxycoumarin form both in DMSO solution, as well as in gas phase; the chroman-2,4-dione form was a minor component. According to X-ray structural analysis data, solid 3-formyl-4-hydroxycoumarin phenylhydrazone exists in the 4-hydroxycoumarin form.

Keywords

arylhydrazones 3-formyl-4-hydroxycoumarin 15N isotope 1H and 13C NMR spectroscopy mass spectrometry tautomerism X-ray structural analysis 

Notes

The authors would like to express their gratitude to Candidate of Chemical Sciences O. S. Anisimova for the consultations regarding the interpretation of mass spectra.

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Copyright information

© Springer Science+Business Media New York 2014

Authors and Affiliations

  • V. S. Lebedev
    • 1
  • B. G. Milevskii
    • 1
  • N. P. Solov’eva
    • 1
  • T. A. Chibisova
    • 1
  • O. N. Kazheva
    • 2
  • O. A. Dyachenko
    • 2
  • G. G. Alexandrov
    • 2
  • V. F. Traven
    • 1
    Email author
  1. 1.D. Mendeleev University of Chemical Technology of RussiaMoscowRussia
  2. 2.Institute of Problems of Chemical PhysicsChernogolovkaRussia

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