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Synthesis of 3,7-disubstituted hexahydro- and tetrahydro-2H-indazoles from cross-conjugated dienones

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Abstract

The oxidation of 3,7-disubstituted hexahydroindazoles with potassium hexacyanoferrate(III) afforded previously unknown tetrahydro-2H-indazole derivatives. A novel ring contraction reaction leading to 2,3-diazaspiro[4.4]non-3-en-1-one derivatives was discovered. The product structure was proved by NMR spectroscopy, mass spectrometry, and X-ray analysis.

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Authors and Affiliations

  1. Faculty of Chemistry, Moscow State University, Leninskie gory 1-3, Moscow, 119991, Russia

    V. N. Nuriev & S. Z. Vatsadze

  2. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Leninskii pr. 47, Moscow, 119991, Russia

    I. A. Vatsadze

  3. MISiS National University of Science and Technology, Leninskii pr. 4, Moscow, 119049, Russia

    N. V. Sviridenkova

Authors
  1. V. N. Nuriev
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  2. I. A. Vatsadze
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  3. N. V. Sviridenkova
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  4. S. Z. Vatsadze
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Correspondence to S. Z. Vatsadze.

Additional information

Original Russian Text © V.N. Nuriev, I.A. Vatsadze, N.V. Sviridenkova, S.Z. Vatsadze, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 3, pp. 409–416.

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Nuriev, V.N., Vatsadze, I.A., Sviridenkova, N.V. et al. Synthesis of 3,7-disubstituted hexahydro- and tetrahydro-2H-indazoles from cross-conjugated dienones. Russ J Org Chem 52, 389–396 (2016). https://doi.org/10.1134/S1070428016030167

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  • DOI: https://doi.org/10.1134/S1070428016030167

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