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New Azepine-Furan Spirocyclic Structures in the Reaction of 4-Aroyl-1,2-dihydrobenzo[d]azepines and 2-Aroyl-4,5-dihydrophenanthreno[1,2-d]azepine with Formaldehyde

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Abstract

4-Aroyl-1,2-dihydrobenzo[d]azepines, as well as their phenanthro[1,2-d]azepine keto analogs, under the action of formaldehyde in the presence of acid-base catalysts, can undergo diastereoselective transformation into spirocyclic systems, containing two spiro-fused hetero rings – tetrahydroazepine and bifunctionalized tetrahydrofuran. This transformation is provided by a combination of azepine-azepine recyclization of substrates followed by spirocyclization of its products.

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Notes

  1. The numbers with one mark indicate the positions in the tetrahydrofuran substituent (in compounds 2a, 2b) or azepine ring (in compounds 2c–2f, 4a, 4b), with two marks (hereinafter)—in the aryl substituent.

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Funding

The synthesis and spectroscopic studies of spirocyclic compounds 2a–2e were performed at the Scientific Research Institute of Physical and Organic Chemistry of the Southern Federal University with financial support from the Russian Foundation for Basic Research (grant no. 20-03-00657/20). The synthesis of compounds 1f, 2f, 4a, and 4b was carried out at the North Caucasian Zonal Veterinary Institute as part of the Program of Fundamental Scientific Research of the State Academies of Sciences for 2019–2021 (topic no. 0710-2019-0044). Spectroscopic and X-ray structural studies were carried out using the equipment of the Collective Use Centers of the South and North Caucasus Federal Universities.

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Authors and Affiliations

  1. North-Caucasian Zonal Research Veterinary Institute, 346406, Novocherkassk, Russia

    A. A. Zubenko, A. N. Bodryakov, L. N. Fetisov, K. N. Kononenko, M. A. Bodryakova & A. I. Klimenko

  2. Institute of Physical and Organic Chemistry, Southern Federal University, 34409, Rostov-on-Don, Russia

    A. S. Morkovnik, L. N. Divaeva & V. S. Sochnev

  3. North-Caucasus Federal University, 355017, Stavropol, Russia

    O. P. Demidov

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  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. S. Sochnev
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  8. K. N. Kononenko
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Correspondence to L. N. Divaeva.

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Additional information

Translated from Zhurnal Obshchei Khimii, 2021, Vol. 91, No. 5, pp. 703–710 https://doi.org/10.31857/S0044460X21050061.

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Zubenko, A.A., Morkovnik, A.S., Divaeva, L.N. et al. New Azepine-Furan Spirocyclic Structures in the Reaction of 4-Aroyl-1,2-dihydrobenzo[d]azepines and 2-Aroyl-4,5-dihydrophenanthreno[1,2-d]azepine with Formaldehyde. Russ J Gen Chem 91, 792–798 (2021). https://doi.org/10.1134/S1070363221050066

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