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Chemistry of Heterocyclic Compounds

, Volume 48, Issue 5, pp 785–794 | Cite as

Chemoselectivity of [4 + 2] cycloaddition in N-maleyl- and N-allyl-2,6-difurylpiperidin-4-ones

  • F. I. ZubkovEmail author
  • E. V. Nikitina
  • V. P. Zaytsev
  • V. N. Khrustalev
  • R. A. Novikov
  • R. S. Borisov
  • A. V. Varlamov
Article

On the basis of a transition state conformation analysis, an attempt was made to explain the high chemoselectivity of intramolecular [4 + 2] cycloaddition in 3-alkyl-2,6-difuryl-N-maleylpiperidin-4-ones. It was shown that the thermal Diels–Alder reaction in these piperidine derivatives takes place through the “boat” conformation and leads to the formation of hydrogenated 1-alkyl-4-(2-furyl)-2H-8,10a-epoxy-pyrido[2,1-a]isoindol-2-ones. The alternative regioisomers, 3-alkyl-4-(2-furyl)-2H-8,10a-epoxy-pyrido[2,1-a]isoindol-2-ones, are hardly formed at all. At the same time, the intramolecular Diels–Alder reaction in the isostructural 3-alkyl-N-allyl-2,6-difurylpiperidin-4-ones, takes place non-regioselectively from the “chair” conformation.

Keywords

3a,6-epoxyisoindole furan furfurylamine piperidin-4-one pyrido[2,1-a]isoindole “boat” conformation intramolecular [4 + 2] cycloaddition intramolecular Diels–Alder reaction stereochemistry 

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Copyright information

© Springer Science+Business Media, Inc. 2012

Authors and Affiliations

  • F. I. Zubkov
    • 1
    Email author
  • E. V. Nikitina
    • 1
  • V. P. Zaytsev
    • 1
  • V. N. Khrustalev
    • 2
  • R. A. Novikov
    • 3
  • R. S. Borisov
    • 4
  • A. V. Varlamov
    • 1
  1. 1.Peoples’ Friendship University of RussiaMoscowRussia
  2. 2.A. N. Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussia
  3. 3.V. A. Engel’gardt Institute of Molecular BiologyRussian Academy of SciencesMoscowRussia
  4. 4.A. V. Topchiev Institute of Petrochemical SynthesisRussian Academy of SciencesMoscowRussia

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