Unexpected Ring Opening During the Imination of Camphor‐Type Bicyclic Ketones
Vladimir V Chernyshov
1, 2, 3, 4
,
Olga I. Yarovaya
1, 2, 3, 4
,
Sergey Z. Vatsadze
5, 6
,
Sophia S. Borisevich
7, 8
,
S N Trukhan
2, 4, 9, 10
,
Yuri V. Gatilov
1, 2, 3, 4
,
Roman Yu Peshkov
2, 4
,
Ilia V. Eltsov
2, 4
,
Oleg N. Martyanov
2, 4, 9, 10
,
Nariman F. Salakhutdinov
1, 2, 3, 4
9
Publication type: Journal Article
Publication date: 2020-12-27
scimago Q2
wos Q2
SJR: 0.558
CiteScore: 4.3
Impact factor: 2.7
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.
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Total citations:
10
Citations from 2024:
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GOST
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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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RIS
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TY - JOUR
DO - 10.1002/ejoc.202001397
UR - https://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.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
PB - Wiley
SP - 452-463
IS - 3
VL - 2021
SN - 1434-193X
SN - 1099-0690
ER -
Cite this
BibTex (up to 50 authors)
Copy
@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://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202001397},
number = {3},
pages = {452--463},
doi = {10.1002/ejoc.202001397}
}
Cite this
MLA
Copy
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://chemistry-europe.onlinelibrary.wiley.com/doi/10.1002/ejoc.202001397.