Chemistry of Heterocyclic Compounds

, Volume 55, Issue 4–5, pp 359–366 | Cite as

N-Difluoromethylation of monosubstituted polydentate azoles

  • Kirill I. PetkoEmail author
  • Taras M. Sokolenko
  • Andrey A. Filatov
  • Vitaliy V. Polovinko
  • Eduard B. Rusanov
  • Vadim A. Dudko
  • Yurii L. Yagupolskii

This study was focused on N-difluoromethylation of monosubstituted polydentate azoles (imidazoles, pyrazoles, and 1,2,4-triazoles) having two or three reactive sites. The substituent effects and role of reaction conditions in determining the product ratio was explored. In the majority of cases, the obtained mixtures of isomers were separated. The target products containing halogen substituents, amino or carboxy groups in the ring can serve as valuable starting compounds in the synthesis of practically useful products.


imidazoles pyrazoles 1,2,4-triazoles difluoromethylation separation of isomers 


The authors would like to express their gratitude to the glassblower Valery Ilyich Lazarev for the design and fabrication of an exclusive “vortex” distillation column that enabled separating small amounts of liquids with close boiling points.

Supplementary material

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ESM 1 (PDF 7788 kb)


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Copyright information

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

Authors and Affiliations

  • Kirill I. Petko
    • 1
    Email author
  • Taras M. Sokolenko
    • 1
  • Andrey A. Filatov
    • 1
  • Vitaliy V. Polovinko
    • 2
  • Eduard B. Rusanov
    • 1
  • Vadim A. Dudko
    • 2
  • Yurii L. Yagupolskii
    • 1
  1. 1.Institute of Organic ChemistryNational Academy of Sciences of UkraineKyivUkraine
  2. 2.Enamine Ltd.KyivUkraine

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