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Features of 3-amino-5-methylisoxazole in heterocyclizations involving pyruvic acids

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Chemistry of Heterocyclic Compounds Aims and scope

The chemical properties of 3-amino-5-methylisoxazole in the reactions involving pyruvic acid derivatives are reported. The multicomponent condensation of 3-amino-5-methylisoxazole, aromatic aldehyde, and pyruvic acid was not effective while the treatment of the starting amine with pyruvic acid derivatives led to suitable synthetic procedures for selective synthesis of furanones and pyrrolones. It was established that only NH2-nucleophilic center of 3-amino-5-methylisoxazole takes part in the heterocyclizations with pyruvic acid derivatives.

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Authors and Affiliations

  1. Division of Chemistry of Functional Materials, State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv, 61072, Ukraine

    Alisa D. Morozova, Elena A. Muravyova, Svitlana V. Shishkina, Vladimir I. Musatov, Sergey M. Desenko & Valentyn A. Chebanov

  2. Faculty of Chemistry, V. N. Karazin Kharkiv National University, 4 Svobody Sq., Kharkiv, 61077, Ukraine

    Svitlana V. Shishkina, Sergey M. Desenko & Valentyn A. Chebanov

  3. Department of Chemistry, University of Konstanz, 10 Universitaetsstrasse, Konstanz, 78467, Germany

    Dmytro Sysoiev

  4. Institute of Chemistry, University of Graz, 1/4 Schubertstraße, Graz, 8010, Austria

    Toma Glasnov

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  1. Alisa D. Morozova
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  2. Elena A. Muravyova
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  3. Svitlana V. Shishkina
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  4. Dmytro Sysoiev
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  6. Vladimir I. Musatov
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  7. Sergey M. Desenko
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  8. Valentyn A. Chebanov
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Correspondence to Valentyn A. Chebanov.

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Published in Khimiya Geterotsiklicheskikh Soedinenii, 2019, 55(1), 78–89

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Morozova, A.D., Muravyova, E.A., Shishkina, S.V. et al. Features of 3-amino-5-methylisoxazole in heterocyclizations involving pyruvic acids. Chem Heterocycl Comp 55, 78–89 (2019). https://doi.org/10.1007/s10593-019-02422-8

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  • DOI: https://doi.org/10.1007/s10593-019-02422-8

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