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Chemistry of Heterocyclic Compounds

, Volume 53, Issue 12, pp 1294–1301 | Cite as

Synthesis of 6-hydroxy-5,6-dihydro-2-pyrones and -pyridones by reaction of 4-aryl-6-trifluoromethyl-2-pyrones with water, hydrazine, and hydroxylamine

  • Sergey A. UsachevEmail author
  • Boris I. Usachev
  • Vyacheslav Ya. Sosnovskikh
Article

Reactions of 4-aryl-6-trifluoromethyl-2H-pyran-2-ones with sodium hydroxide followed by acidification provided the respective 6-hydroxy-5,6-dihydro derivatives, while the reactions of 4-aryl-6-trifluoromethyl-2H-pyran-2-ones with hydrazine and hydroxylamine were accompanied by rearrangement to N-substituted 6-hydroxy-5,6-dihydro-2-pyridones.

Keywords

2-pyrones 5,6-dihydro-2-pyridones 5,6-dihydro-2-pyrones ANRORC rearrangement 

Notes

This work was performed with financial support from the Russian Foundation for Basic Research (grant No. 1703-00340).

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© Springer Science+Business Media, LLC, part of Springer Nature 2018

Authors and Affiliations

  • Sergey A. Usachev
    • 1
    Email author
  • Boris I. Usachev
    • 2
  • Vyacheslav Ya. Sosnovskikh
    • 1
  1. 1.Institute of Natural Sciences and MathematicsUral Federal University named after the first President of Russia B. N. YeltsinYekaterinburgRussia
  2. 2.Department of Chemistry, School of Pure Sciences, College of Engineering, Science & TechnologyFiji National UniversityLautokaFiji

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