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N-Difluoromethylation of monosubstituted polydentate azoles

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Chemistry of Heterocyclic Compounds Aims and scope

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.

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References

  1. Kirk, K. L. Org. Proc. Res. Dev. 2008, 12, 305.

    Article  CAS  Google Scholar 

  2. Fluorinated Heterocyclic Compounds: Synthesis, Chemistry and application; Petrov, V. A., Ed.; John Wiley & Sons: Hoboken, 2009, p. 100, 138, 141.

  3. Erickson, J. A.; McLoughlin, J. I. J. Org. Chem. 1995, 60, 1626.

    Article  CAS  Google Scholar 

  4. Sato, N.; Ando, M.; Ishikawa, S.; Nagase, T.; Nagai, K.; Kanatani, A. WO Patent 2004/031175.

  5. Yu, G; Rao, P. N. P.; Chowdhury, M. A.; Abdellatif, K. R. A.; Dong, Y.; Das, D.; Velazquez, C. A.; Suresh, M. R.; Knaus, E. E. Bioorg. Med. Chem. Lett. 2010, 20, 2168.

    Article  CAS  PubMed  Google Scholar 

  6. Dayan, B. E.; Armstrong, B. M.; Weete, G. D. J. Agric. Food Chem. 1998, 46, 2024.

    Article  CAS  Google Scholar 

  7. Elmarakby, S. A.; Supplee, D.; Cook, R. J. Agric. Food Chem. 2001, 49, 5285.

    Article  CAS  PubMed  Google Scholar 

  8. Kobayashi, O; Takatsuna, R.; Niikura, N.; Matsukawa, T.; Nakamura, S.; Hirai, K.; Koshi, S.; Kawanishi, N.; Yamada, O. JP Patent 201656157 A.

  9. Thomoson, C. S.; Wang, L.; Dolbier, W. R. J. Fluorine Chem. 2014, 168, 34.

    Article  CAS  Google Scholar 

  10. Ni, C.; Hu, J. Synthesis 2014, 842.

  11. Lu, Y.; Liu, C.; Chen Q-Y. Curr. Org. Chem. 2015, 19, 1638.

    Article  CAS  Google Scholar 

  12. Yierien, D. E.; Barata-Vallejo, S.; Postigo, A. Chem.–Eur. J. 2017, 23, 14676.

    Article  CAS  Google Scholar 

  13. Joncryk, A.; Nawrot, E.; Kisielewski, M. J. Fluorine Chem. 2005, 126, 1587.

    Article  CAS  Google Scholar 

  14. Li, L.; Wang, F.; Ni, C.; Hu, S. Angew. Chem., Int. Ed. 2013, 52, 12390.

    Article  CAS  Google Scholar 

  15. Petko, K. I.; Yagupolskii, L. M. J. Fluorine Chem. 2001, 108, 211.

    Article  CAS  Google Scholar 

  16. Fuchibe, K.; Koseki, Y.; Aono, T.; Sasagawa, H.; Ishikawa, S. J. Fluorine Chem. 2012, 153, 52.

    Article  CAS  Google Scholar 

  17. Prakash, G. K. S.; Krishnamoorty S.; Ganesh, S. K.; Kulkarni, A.; Haiges, R.; Olah, G. A. Org. Lett. 2014, 16, 54.

    Article  CAS  PubMed  Google Scholar 

  18. Petko, K. I. J. Fluorine Chem. 2018, 205, 5.

    Article  CAS  Google Scholar 

  19. Methods for quantitative organic elemental analysis [in Russian]; Gel'man, N. E., Ed.; Khimiya: Moscow, 1987.

  20. Sheldrick, G. Acta Crystallogr., Sect. A: Found. Crystallogr. 2008, A64, 112.

    Article  CAS  Google Scholar 

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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.

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Correspondence to Kirill I. Petko.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(4/5), 359–366

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Petko, K.I., Sokolenko, T.M., Filatov, A.A. et al. N-Difluoromethylation of monosubstituted polydentate azoles. Chem Heterocycl Comp 55, 359–366 (2019). https://doi.org/10.1007/s10593-019-02465-x

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  • DOI: https://doi.org/10.1007/s10593-019-02465-x

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