Synthesis of fluorinated 2,6-heptanediones and 2-oxa-6- azabicyclo[2.2.2]octanes from 1,4-dihydropyridines

Nadiia V. Pikun, Natalya P. Kolesnyk, Eduard B. Rusanov, Aiva Plotniece, Martins Rucins, Arkadij Sobolev, Yuriy G. Shermolovich (Coresponding Author)

Research output: Contribution to journalArticlepeer-review

3 Citations (Scopus)


Electrophilic fluorination of Hantzsch-type 1,4-dihydropyridines with Selectfluor® led to the formation of new fluorinated 2,6-heptanediones - dialkyl 2,4-diacetyl-2,4-difluoro-3-phenylpentanedioates. Novel 2,6-heptanedione derivatives in reaction with hydrazine hydrate easily form 6-amino-4,7-difluoro-3-hydroxy-1,3-dimethyl-5-oxo-8-phenyl-2-oxa-6-azabicyclo[2.2.2]octanes instead of the corresponding diazepine derivatives. The obtained 2-оxa-6-azabicyclo[2,2,2]octanes are thermally stable at the temperatures below 50°С. At higher temperatures rearrangement of 2-oxa-6-azabicyclo[2,2,2]octanes offers new fluorine-containing pyrazolinone derivatives - alkyl esters of 2-fluoro-2-((4-fluoro-3-methyl-5-oxo-4,5-dihydro-1H-pyrazol-4-yl)(phenyl)methyl)-3-oxobutanoates.

Original languageEnglish
Pages (from-to)2884-2890
Number of pages7
Issue number23
Publication statusPublished - 7 Jun 2018
Externally publishedYes


  • 1,4-Dihydropyridines
  • 2,4-Diacetyl-2,4-difluoro-3-phenylpentanedioates
  • 2-Oxa-6-azabicyclo[2.2.2]octanes
  • Electrophilic fluorination
  • Selectfluor

Field of Science*

  • 1.4 Chemical sciences
  • 3.1 Basic medicine

Publication Type*

  • 1.1. Scientific article indexed in Web of Science and/or Scopus database


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