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Decarboxylation and electrophilic substitution in 3-tert-butyl-4-oxopyrazolo[5,1-c][1,2,4]triazines

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Abstract

Reactivity of 7-R-3-tert-butyl-4-oxo-4,6-dihydropyrazolo[5,1-c][1,2,4]triazine-8-carboxylic acids (R = NH2, N3, H) and products of their decarboxylation towards different electrophilic agents (chloroacetone, Boc2O/NaN3, DMF/POCl3, TMSBr, N-halosuccinimides, and HNO2) was studied. A selective synthesis of new C(7),C(8)-functionalized and N(1)-tert-butyloxycarbonyl-substituted 4-oxopyrazolo[5,1-c][1,2,4]triazines was performed. The structures of the synthesized compounds were confirmed by IR and NMR spectroscopy, high resolution mass spectrometry and single crystal X-ray diffraction analysis.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    S. M. Ivanov & A. M. Shestopalov

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 119991, Moscow, Russian Federation

    K. A. Lyssenko

  3. M. V. Lomonosov Moscow State University, 1 Leninskie Gory, 119991, Moscow, Russian Federation

    K. A. Lyssenko

  4. Southwest State University, 94 ul. 50 Let Oktabrya, 305040, Kursk, Russian Federation

    L. M. Mironovich

Authors
  1. S. M. Ivanov
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  2. K. A. Lyssenko
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  3. L. M. Mironovich
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  4. A. M. Shestopalov
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Correspondence to S. M. Ivanov.

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Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 9, pp. 1714–1722, September, 2019.

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Ivanov, S.M., Lyssenko, K.A., Mironovich, L.M. et al. Decarboxylation and electrophilic substitution in 3-tert-butyl-4-oxopyrazolo[5,1-c][1,2,4]triazines. Russ Chem Bull 68, 1714–1722 (2019). https://doi.org/10.1007/s11172-019-2615-z

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  • DOI: https://doi.org/10.1007/s11172-019-2615-z

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