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Synthesis of 3-tert-Butyl-4-hydroxy-1,4-dihydropyrazolo[5,1-c][1,2,4]triazines

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Abstract

Two new approaches have been proposed for the synthesis of 4-hydroxy-1,4-dihydropyrazolo[5,1-c]-[1,2,4]triazines via (1) borohydride reduction of 1-R-4-oxo-1,4-dihydro derivatives and (2) Vilsmeier formylation of 3-tert-butyl-8-methylpyrazolo[5,1-c][1,2,4]triazine. 3-tert-Butylpyrazolo[5,1-c][1,2,4]triazin-1(5)-ium cation has been generated for the first time by treatment of 7-amino-1-benzyl-3-tert-butyl-4-hydroxy-1,4-dihydropyrazolo[5,1-c][1,2,4]triazine-8-carbonitrile with trifluoroacetic acid in CDCl3. The hydrolysis of 4-alkoxy-1,4-dihydropyrazolo[5,1-c][1,2,4]triazines was monitored by 1H and 13C NMR spectroscopy. The structure of the synthesized compounds was confirmed by spectral and X-ray diffraction data.

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Authors and Affiliations

  1. Southwest State University, 305040, Kursk, Russia

    L. M. Mironovich

  2. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russia

    S. M. Ivanov & N. G. Kolotyrkina

  3. Mendeleev University of Chemical Technology of Russia, 125047, Moscow, Russia

    S. M. Ivanov

Authors
  1. L. M. Mironovich
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  2. S. M. Ivanov
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  3. N. G. Kolotyrkina
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Correspondence to L. M. Mironovich.

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Mironovich, L.M., Ivanov, S.M. & Kolotyrkina, N.G. Synthesis of 3-tert-Butyl-4-hydroxy-1,4-dihydropyrazolo[5,1-c][1,2,4]triazines. Russ J Org Chem 56, 596–603 (2020). https://doi.org/10.1134/S1070428020040065

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