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Russian Journal of Organic Chemistry

, Volume 55, Issue 1, pp 74–82 | Cite as

Pyridine—Azepine Structural Modification of 3,4-Dihydro-nor-isoharmine

  • A. A. Zubenko
  • A. S. MorkovnikEmail author
  • L. N. Divaeva
  • V. G. Kartsev
  • A. A. Anisimov
  • K. Yu. Suponitsky
Article
  • 4 Downloads

Abstract

Structural modification of 3,4-dihydro-nor-isoharmine through expansion of the dihydropyridine ring to dihydroazepine was accomplished in two stages including pyridine-azepine recyclization of the quaternized substrate by the action of phenacyl halides and their heterocyclic analogs. The recyclization process can be accompanied by 1,2-migration of the acyl group to give mixtures of 4-acyl-9-methoxy-3-methyl-1,2-dihydroazepino[4,5-b]indoles and their 5-acyl-substituted isomers. Factor influencing the recyclization direction and product ratio were analyzed.

Keywords

3,4-dihydro-nor-isoharmine recyclization 1,2-acyl rearrangement 4(5)-acyl-9-methoxy-3-methyl-1,2-dihydroazepino[4,5-b]indoles 

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Copyright information

© Pleiades Publishing, Ltd. 2019

Authors and Affiliations

  • A. A. Zubenko
    • 1
  • A. S. Morkovnik
    • 2
    Email author
  • L. N. Divaeva
    • 2
  • V. G. Kartsev
    • 3
  • A. A. Anisimov
    • 4
  • K. Yu. Suponitsky
    • 5
  1. 1.North Caucasus Zonal Research Veterinary Institute, Rostovskoe shosseNovocherkassk, Rostov oblastRussia
  2. 2.Institute of Physical and Organic ChemistrySouthern Federal UniversityRostov-on-DonRussia
  3. 3.InterBioScreen Ltd.Chernogolovka, Moscow oblastRussia
  4. 4.Mendeleev University of Chemical Technology of RussiaMoscowRussia
  5. 5.Nesmeyanov Institute of Organoelement CompoundsRussian Academy of SciencesMoscowRussia

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