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Reactions of 3,3-dialkyl-2,3-dihydro-6-trifluoromethyl-4-pyrones with hydroxylamine. Synthesis and structures of 5-(1,1-dialkyl-2-hydroxyethyl)-5-hydroxy-3-trifluoromethyl-Δ2-isoxazolines

  • Organic Chemistry
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Russian Chemical Bulletin Aims and scope

Abstract

The reactions of 3,3-dialkyl-2,3-dihydro-6-trifluoromethyl-4-pyrones with hydroxylamine hydrochloride afforded regioisomeric 3(5)-(1,1-dialkyl-2-hydroxyethyl)-5-hydroxy-5(3)-trifluoromethyl-Δ2-isoxazolines depending on the reaction conditions. The title compounds were also prepared from 2,2-dialkyl-5-amino-1-hydroxy-6,6,6-trifluorohex-4-en-3-ones. The above dihydropyrones reacted with hydroxylamine (base) to yield 3-(1,1-dialkyl-2-hydroxyethyl)-5-hydroxy-5-trifluoromethyl-Δ2-isoxazolines.

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Authors and Affiliations

  1. A. M. Gorky Ural State University, 51 prosp. Lenina, 620083, Ekaterinburg, Russian Federation

    V. Ya. Sosnovskikh & M. Yu. Mel'nikov

  2. A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, 28 ul. Vavilova, 117813, Moscow, Russian Federation

    S. A. Pogozhikh

Authors
  1. V. Ya. Sosnovskikh
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  2. M. Yu. Mel'nikov
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  3. S. A. Pogozhikh
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Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 7, pp. 1334–1339, July, 1999.

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Sosnovskikh, V.Y., Mel'nikov, M.Y. & Pogozhikh, S.A. Reactions of 3,3-dialkyl-2,3-dihydro-6-trifluoromethyl-4-pyrones with hydroxylamine. Synthesis and structures of 5-(1,1-dialkyl-2-hydroxyethyl)-5-hydroxy-3-trifluoromethyl-Δ2-isoxazolines. Russ Chem Bull 48, 1323–1328 (1999). https://doi.org/10.1007/BF02495297

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  • DOI: https://doi.org/10.1007/BF02495297

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