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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
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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.

Keywords

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 

Notes

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.

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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

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