Pyridine—Azepine Structural Modification of 3,4-Dihydro-nor-isoharmine
A A Zubenko
1
,
A S Morkovnik
2
,
L N Divaeva
2
,
V G Kartsev
3
,
A.A. Anisimov
4
,
K Yu Suponitsky
5
1
North Caucasus Zonal Research Veterinary Institute, Rostovskoe shosse, Novocherkassk, Rostov oblast, Russia
|
3
InterBioScreen Ltd., Chernogolovka, Moscow oblast, Russia
|
Publication type: Journal Article
Publication date: 2019-01-01
scimago Q4
wos Q4
SJR: 0.190
CiteScore: 1.3
Impact factor: 0.9
ISSN: 10704280, 16083393
Organic Chemistry
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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Zubenko A. A. et al. Pyridine—Azepine Structural Modification of 3,4-Dihydro-nor-isoharmine // Russian Journal of Organic Chemistry. 2019. Vol. 55. No. 1. pp. 74-82.
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Zubenko A. A., Morkovnik A. S., Divaeva L. N., Kartsev V. G., Anisimov A., Suponitsky K. Yu. Pyridine—Azepine Structural Modification of 3,4-Dihydro-nor-isoharmine // Russian Journal of Organic Chemistry. 2019. Vol. 55. No. 1. pp. 74-82.
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RIS
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TY - JOUR
DO - 10.1134/s1070428019010081
UR - https://doi.org/10.1134/s1070428019010081
TI - Pyridine—Azepine Structural Modification of 3,4-Dihydro-nor-isoharmine
T2 - Russian Journal of Organic Chemistry
AU - Zubenko, A A
AU - Morkovnik, A S
AU - Divaeva, L N
AU - Kartsev, V G
AU - Anisimov, A.A.
AU - Suponitsky, K Yu
PY - 2019
DA - 2019/01/01
PB - Pleiades Publishing
SP - 74-82
IS - 1
VL - 55
SN - 1070-4280
SN - 1608-3393
ER -
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@article{2019_Zubenko,
author = {A A Zubenko and A S Morkovnik and L N Divaeva and V G Kartsev and A.A. Anisimov and K Yu Suponitsky},
title = {Pyridine—Azepine Structural Modification of 3,4-Dihydro-nor-isoharmine},
journal = {Russian Journal of Organic Chemistry},
year = {2019},
volume = {55},
publisher = {Pleiades Publishing},
month = {jan},
url = {https://doi.org/10.1134/s1070428019010081},
number = {1},
pages = {74--82},
doi = {10.1134/s1070428019010081}
}
Cite this
MLA
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Zubenko, A. A., et al. “Pyridine—Azepine Structural Modification of 3,4-Dihydro-nor-isoharmine.” Russian Journal of Organic Chemistry, vol. 55, no. 1, Jan. 2019, pp. 74-82. https://doi.org/10.1134/s1070428019010081.