Email this article 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
- Authors: Tkachenko I.V.1, Tarabara I.N.2, Omel’chenko I.V.3, Pal’chikov V.A.2,4
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Affiliations:
- R&D Enterprise “Enamine Ltd.,”
- Oles’ Honchar Dnepropetrovsk National University
- State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine
- Peoples’ Friendship University of Russia
- Issue: Vol 52, No 5 (2016)
- Pages: 661-669
- Section: Article
- URL: https://journal-vniispk.ru/1070-4280/article/view/214289
- DOI: https://doi.org/10.1134/S1070428016050080
- ID: 214289
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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.
About the authors
I. V. Tkachenko
R&D Enterprise “Enamine Ltd.,”
Email: palchikoff@mail.ru
Ukraine, Kiev
I. N. Tarabara
Oles’ Honchar Dnepropetrovsk National University
Email: palchikoff@mail.ru
Ukraine, pr. Gagarina 72, Dnepropetrovsk, 49010
I. V. Omel’chenko
State Scientific Institution “Institute for Single Crystals” of National Academy of Sciences of Ukraine
Email: palchikoff@mail.ru
Ukraine, Kharkiv
V. A. Pal’chikov
Oles’ Honchar Dnepropetrovsk National University; Peoples’ Friendship University of Russia
Author for correspondence.
Email: palchikoff@mail.ru
Ukraine, pr. Gagarina 72, Dnepropetrovsk, 49010; Moscow
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