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Reactivity of 5-endo-hydroxy-4-azatricyclo[5.2.1.02,6]dec-8-en-3-ones and their isomerization initiated by acids and bases

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Abstract

Study of isomerization of 5-endo-hydroxy-4-azatricyclo[5.2.1.02,6]dec-8-en-3-ones under the action of Lewis acids (MgBr2, AlCl3), CF3COOH, and NaH showed that the optimum catalyst of the process was trifluoroacetic acid. In reaction of 4-benzyl-5-endo-hydroxy-4-azatricyclo-[5.2.1.02,6]dec-8-en-3-one with anhydrous AlCl3 in benzene was unexpectedly isolated N-benzyl-3-(diphenylmethyl)bicyclo[2.2.1]hept-5-ene-2-carboxamide. A convenient method was developed for the preparation of 5-exo-alkoxy-4-alkyl(aryl)-4-azatricyclo[5.2.1.02,6]dec- 8-en-3-ones.

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Authors and Affiliations

  1. R&D Enterprise “Enamine Ltd.,”, Kiev, Ukraine

    I. V. Tkachenko

  2. Oles’ Honchar Dnepropetrovsk National University, pr. Gagarina 72, Dnepropetrovsk, 49010, Ukraine

    I. N. Tarabara & V. A. Pal’chikov

  3. State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine, Kharkiv, Ukraine

    I. V. Omel’chenko

  4. Peoples’ Friendship University of Russia, Moscow, Russia

    V. A. Pal’chikov

Authors
  1. I. V. Tkachenko
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  2. I. N. Tarabara
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  3. I. V. Omel’chenko
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  4. V. A. Pal’chikov
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Corresponding author

Correspondence to V. A. Pal’chikov.

Additional information

Original Russian Text © I.V. Tkachenko, I.N. Tarabara, I.V. Omel’chenko, V.A. Pal’chikov, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 5, pp. 676–684.

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Tkachenko, I.V., Tarabara, I.N., Omel’chenko, I.V. et al. Reactivity of 5-endo-hydroxy-4-azatricyclo[5.2.1.02,6]dec-8-en-3-ones and their isomerization initiated by acids and bases. Russ J Org Chem 52, 661–669 (2016). https://doi.org/10.1134/S1070428016050080

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  • DOI: https://doi.org/10.1134/S1070428016050080

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