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Synthesis of (3-tert-Butylpyrazolo[5,1-c][1,2,4]triazin-4-yl)phosphine Oxides

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Abstract

Aromatic 7-R1-8-R2-3-tert-butylpyrazolo[5,1-c][1,2,4]triazines (R1 = H, Br; R2 = H, Me, Br) reacted with lithium diphenyl- and methyl(phenyl)phosphides in THF at lower temperature to give nucleophilic addition products to the C4 atom. Further oxidation with atmospheric oxygen or N-bromosuccinimide afforded previously unknown (3-tert-butylpyrazolo[5,1-c][1,2,4]triazin-4-yl)phosphine oxides and 2,2-dibromoacetamide as a by-product. The structure of the isolated compounds was confirmed by IR, 1H, 13C, and 31P NMR, and mass spectra and X-ray analysis.

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ACKNOWLEDGMENTS

The X-ray diffraction study was performed at the Structural Studies Department, Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences.

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Authors and Affiliations

  1. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Moscow, Russia

    S. M. Ivanov, N. G. Kolotyrkina & M. E. Minyaev

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

    S. M. Ivanov

  3. Southwest State University, 305040, Kursk, Russia

    L. M. Mironovich

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Ivanov, S.M., Mironovich, L.M., Kolotyrkina, N.G. et al. Synthesis of (3-tert-Butylpyrazolo[5,1-c][1,2,4]triazin-4-yl)phosphine Oxides. Russ J Org Chem 57, 47–57 (2021). https://doi.org/10.1134/S1070428021010073

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