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Chemistry of Heterocyclic Compounds

, Volume 49, Issue 5, pp 746–759 | Cite as

Synthesis of Epoxyisoindolo[1,2-a]isoquinolinium Salts by an Intramolecular [2+4] Cycloaddition Reaction in 2-Allyl-1-furylisoquinolinium Halides

  • F. I. Zubkov
  • V. P. ZaytsevEmail author
  • M. D. Obushak
  • Yu. D. Ershova
  • D. F. Mertsalov
  • E. A. Sorokina
  • E. V. Nikitina
  • Yu. I. Gorak
  • R. Z. Lytvyn
  • A. V. Varlamov
Article

We examined the tandem alkylation/[2+4] cycloaddition of 1-(2-furyl)-3,4-dihydroisoquinolines by various allyl halides. It was found that the process occurred through the intermediate formation of 2-allyl-1-furyl-3,4-dihydroisoquinolinium salts with a subsequent intramolecular exo addition of the allyl fragment to the furan ring. The adducts obtained were structural analogs of the isoindolo-[1,2-a]isoquinoline alkaloids jamtine and hirsutine.

Keywords

alkaloids allyl halides furan isoindolo[1,2-a]isoquinolines intramolecular [2+4] cycloaddition 

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Copyright information

© Springer Science+Business Media New York 2013

Authors and Affiliations

  • F. I. Zubkov
    • 1
  • V. P. Zaytsev
    • 1
    Email author
  • M. D. Obushak
    • 2
  • Yu. D. Ershova
    • 1
  • D. F. Mertsalov
    • 1
  • E. A. Sorokina
    • 1
  • E. V. Nikitina
    • 1
  • Yu. I. Gorak
    • 2
  • R. Z. Lytvyn
    • 2
  • A. V. Varlamov
    • 1
  1. 1.Peoples’ Friendship University of RussiaMoscowRussia
  2. 2.Ivan Franko Lviv National UniversityLvivUkraine

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