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.
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, 2018, 54(12), 1168–1171
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Erkin, A.V., Gurzhiy, V.V. & Krutikov, V.I. 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. Chem Heterocycl Comp 54, 1168–1171 (2018). https://doi.org/10.1007/s10593-019-02409-5
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DOI: https://doi.org/10.1007/s10593-019-02409-5