Chemistry of Heterocyclic Compounds

, Volume 54, Issue 12, pp 1168–1171 | Cite as

The potential of employing substituted bis[3-hydroxy-2-(pyrimidin-2-yl)-2Н-pyrazol-4-yl]methane for the synthesis of symmetrical N,O-macroheterocycles with a dioxacycloalkane central fragment

  • Andrei V. ErkinEmail author
  • Vladislav V. Gurzhiy
  • Viktor I. Krutikov

O-cyclialkylation of substituted bis[3-hydroxy-2-(pyrimidin-2-yl)-2H-pyrazol-4-yl]methane by α,ω-dibromoalkanes with a hydrocarbon chain length of up to three CH2 groups has been carried out. A novel pyrazolophane, 1,6-dioxacycloundecane with symmetrically annulated fragments of 1-(pyrimidin-2-yl)-1H-pyrazole, was isolated and characterized as a result of this reaction. The precursor bridged heterocycle was obtained by condensation of the corresponding 2-(pyrimidin-2-yl)-2H-pyrazol-3-ol with formaldehyde in a 2:1 molar ratio.


bis[3-hydroxy-2-(pyrimidin-2-yl)-2Н-pyrazol-4-yl]methane α,ω-dibromoalkanes formaldehyde pyrazolophane 2-(pyrimidin-2-yl)-2H-pyrazol-3-ol condensation O-cyclialkylation 


X-ray structural analysis of single crystals of pyrazolophane 3 was performed at the resource center “X-ray diffraction research methods” of the Saint Petersburg State University.


  1. 1.
    Gouda, M. A. J. Heterocycl. Chem. 2016, 53, 356.Google Scholar
  2. 2.
    Hirano, S.; Hiyama, T.; Fujita, S.; Kawaguti, T.; Hayashi, Y.; Nozaki, H. Tetrahedron 1974, 30, 2633.CrossRefGoogle Scholar
  3. 3.
    Molteni, G. ARKIVOC 2007, (ii), 224.Google Scholar
  4. 4.
    Chande, M. S.; Barve, P. A.; Khanwelkar, R. R.; Athalye, S. S.; Venkataraman, D. S. Can. J. Chem. 2007, 85, 21.CrossRefGoogle Scholar
  5. 5.
    Chande, M. S.; Puthamane, K. A.; Barve, P. A.; Khanwelkar, R. R.; Venkataraman, D. S. J. Braz. Chem. Soc. 2008, 19, 42.CrossRefGoogle Scholar
  6. 6.
    Kotha, S.; Shirbhate, M. E.; Waghule, G. T. Beilstein J. Org. Chem. 2015, 11, 1274.Google Scholar
  7. 7.
    Sano, M.; Itoh, I.; Nakai, Y.; Naito, T. Chem. Pharm. Bull. 1969, 17, 1485.CrossRefGoogle Scholar
  8. 8.
    Kumar, B.; Mahajan, H.; Paul, S.; Kanta, R.; Gupta, V. K. Acta Crystallogr., Sect. E: Crystallogr. Commun. 2015, 71, o805.Google Scholar
  9. 9.
    Chande, M. S.; Godbole, A. A.; Coutinhob, E.; Desai, P. Indian J. Chem., Sect. B: Org. Chem. Incl. Med Chem. 2003, 42, 397.Google Scholar
  10. 10.
    Khalil, A. Kh.; Hassan, M. A.; Mohamed, M. M.; El-Sayed, A. M. Phosphorus, Sulfur Silicon Relat. Elem. 2005, 180, 479.Google Scholar
  11. 11.
    Gordon, А.; Ford, R. Chemist's Companion [Russian translation]; Mir: Moscow, 1976.Google Scholar
  12. 12.
    Erkin, А. V.; Krutikov, V. I.; Baklanova, E. G. Khim. prom. 2012, 89, 217.Google Scholar
  13. 13.
    CrysAlisPro, Version; Rigaku Oxford Diffraction, 2017.Google Scholar
  14. 14.
    Sheldrick, G. M. Acta Crystallogr., Sect. A: Found Crystallogr. 2008, A64, 112.Google Scholar
  15. 15.
    Sheldrick, G. M. Acta Crystallogr., Sect С: Struct. Chem. 2015, C71, 3.Google Scholar
  16. 16.
    Dolomanov, O. V.; Bourhis, L. J.; Gildea, R. J.; Howard, J. A. K.; Puschmann, H. J. Appl. Crystallogr. 2009, 42, 339.CrossRefGoogle Scholar

Copyright information

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

Authors and Affiliations

  • Andrei V. Erkin
    • 1
    Email author
  • Vladislav V. Gurzhiy
    • 2
  • Viktor I. Krutikov
    • 1
  1. 1.Saint Petersburg State Institute of Technology (Technical University)Saint PetersburgRussia
  2. 2.Saint Petersburg State UniversitySaint PetersburgRussia

Personalised recommendations