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

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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.

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Authors and Affiliations

  1. North Caucasus Zonal Research Veterinary Institute, Rostovskoe shosse, Novocherkassk, Rostov oblast, 346421, Russia

    A. A. Zubenko

  2. Institute of Physical and Organic Chemistry, Southern Federal University, pr. Stachki 194/2, Rostov-on-Don, 344090, Russia

    A. S. Morkovnik & L. N. Divaeva

  3. InterBioScreen Ltd., Institutskii pr. 7, Chernogolovka, Moscow oblast, 142432, Russia

    V. G. Kartsev

  4. Mendeleev University of Chemical Technology of Russia, Miusskaya pl. 9, Moscow, 125047, Russia

    A. A. Anisimov

  5. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, Moscow, 119991, Russia

    K. Yu. Suponitsky

Authors
  1. A. A. Zubenko
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  2. A. S. Morkovnik
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  3. L. N. Divaeva
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  4. V. G. Kartsev
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  5. A. A. Anisimov
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  6. K. Yu. Suponitsky
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Corresponding author

Correspondence to A. S. Morkovnik.

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Zubenko, A.A., Morkovnik, A.S., Divaeva, L.N. et al. Pyridine—Azepine Structural Modification of 3,4-Dihydro-nor-isoharmine. Russ J Org Chem 55, 74–82 (2019). https://doi.org/10.1134/S1070428019010081

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  • DOI: https://doi.org/10.1134/S1070428019010081

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