European Journal of Organic Chemistry, volume 2021, issue 3, pages 452-463
Unexpected Ring Opening During the Imination of Camphor‐Type Bicyclic Ketones
Chernyshov Vladimir V
1, 2
,
Yarovaya Olga I.
1, 2
,
Trukhan S N
2, 5
,
Gatilov Yuri V.
1, 2
,
Peshkov Roman Yu
2
,
Eltsov Ilia V.
2
,
Martyanov Oleg N.
2, 5
,
Publication type: Journal Article
Publication date: 2020-12-27
Quartile SCImago
Q2
Quartile WOS
Q2
Impact factor: 2.8
ISSN: 1434193X, 10990690
Organic Chemistry
Physical and Theoretical Chemistry
Abstract
A new ring opening reaction was found while attempting to isolate the imines from ortho‐heteroatom substituted anilines and camphor‐like bicyclic ketones. The benzoazoles containing a cyclopentanemethyl group at position 2 of the heterocycle were isolated instead of the expected imines. The detailed study of the transformation, including EPR experiments, revealed the most probable radical mechanism. The proposed reaction pathways were confirmed by quantum chemical calculations. The dichotomy of 1–2 and 2–3 bonds cleavage is discussed together with the evaluation of the stereochemical outcome of the reactions. The benzoazoles obtained via the new reaction are of particular interest for the medicinal chemistry.
Citations by journals
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1
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Chemistry of Heterocyclic Compounds
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Chemistry of Heterocyclic Compounds
1 publication, 20%
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Topics in Current Chemistry
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1 publication, 20%
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Inorganic Chemistry
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1 publication, 20%
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Chemical Communications
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1 publication, 20%
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Doklady Chemistry
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Doklady Chemistry
1 publication, 20%
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1
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Citations by publishers
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1
2
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Springer Nature
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Springer Nature
2 publications, 40%
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American Chemical Society (ACS)
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American Chemical Society (ACS)
1 publication, 20%
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Royal Society of Chemistry (RSC)
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Royal Society of Chemistry (RSC)
1 publication, 20%
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Pleiades Publishing
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Pleiades Publishing
1 publication, 20%
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1
2
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Chernyshov V. V. et al. Unexpected Ring Opening During the Imination of Camphor‐Type Bicyclic Ketones // European Journal of Organic Chemistry. 2020. Vol. 2021. No. 3. pp. 452-463.
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Chernyshov V. V., Yarovaya O. I., Vatsadze S. Z., Borisevich S. S., Trukhan S. N., Gatilov Y. V., Peshkov R. Yu., Eltsov I. V., Martyanov O. N., Salakhutdinov N. F. Unexpected Ring Opening During the Imination of Camphor‐Type Bicyclic Ketones // European Journal of Organic Chemistry. 2020. Vol. 2021. No. 3. pp. 452-463.
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TY - JOUR
DO - 10.1002/ejoc.202001397
UR - https://doi.org/10.1002%2Fejoc.202001397
TI - Unexpected Ring Opening During the Imination of Camphor‐Type Bicyclic Ketones
T2 - European Journal of Organic Chemistry
AU - Chernyshov, Vladimir V
AU - Yarovaya, Olga I.
AU - Vatsadze, Sergey Z.
AU - Borisevich, Sophia S.
AU - Trukhan, S N
AU - Gatilov, Yuri V.
AU - Peshkov, Roman Yu
AU - Eltsov, Ilia V.
AU - Martyanov, Oleg N.
AU - Salakhutdinov, Nariman F.
PY - 2020
DA - 2020/12/27 00:00:00
PB - Wiley
SP - 452-463
IS - 3
VL - 2021
SN - 1434-193X
SN - 1099-0690
ER -
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@article{2020_Chernyshov,
author = {Vladimir V Chernyshov and Olga I. Yarovaya and Sergey Z. Vatsadze and Sophia S. Borisevich and S N Trukhan and Yuri V. Gatilov and Roman Yu Peshkov and Ilia V. Eltsov and Oleg N. Martyanov and Nariman F. Salakhutdinov},
title = {Unexpected Ring Opening During the Imination of Camphor‐Type Bicyclic Ketones},
journal = {European Journal of Organic Chemistry},
year = {2020},
volume = {2021},
publisher = {Wiley},
month = {dec},
url = {https://doi.org/10.1002%2Fejoc.202001397},
number = {3},
pages = {452--463},
doi = {10.1002/ejoc.202001397}
}
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MLA
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Chernyshov, Vladimir V., et al. “Unexpected Ring Opening During the Imination of Camphor‐Type Bicyclic Ketones.” European Journal of Organic Chemistry, vol. 2021, no. 3, Dec. 2020, pp. 452-463. https://doi.org/10.1002%2Fejoc.202001397.