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Unexpected Ring Opening During the Imination of Camphor-Type Bicyclic Ketones. / Chernyshov, Vladimir V.; Yarovaya, Olga I.; Vatsadze, Sergey Z. et al.

In: European Journal of Organic Chemistry, Vol. 2021, No. 3, 22.01.2021, p. 452-463.

Research output: Contribution to journal › Article › peer-review

Harvard

Chernyshov, VV, Yarovaya, OI, Vatsadze, SZ, Borisevich, SS, Trukhan, SN, Gatilov, YV, Peshkov, RY, Eltsov, IV, Martyanov, ON & Salakhutdinov, NF 2021, 'Unexpected Ring Opening During the Imination of Camphor-Type Bicyclic Ketones', European Journal of Organic Chemistry, vol. 2021, no. 3, pp. 452-463. https://doi.org/10.1002/ejoc.202001397

APA

Chernyshov, V. V., Yarovaya, O. I., Vatsadze, S. Z., Borisevich, S. S., Trukhan, S. N., Gatilov, Y. V., Peshkov, R. Y., Eltsov, I. V., Martyanov, O. N., & Salakhutdinov, N. F. (2021). Unexpected Ring Opening During the Imination of Camphor-Type Bicyclic Ketones. European Journal of Organic Chemistry, 2021(3), 452-463. https://doi.org/10.1002/ejoc.202001397

Vancouver

Chernyshov VV, Yarovaya OI, Vatsadze SZ, Borisevich SS, Trukhan SN, Gatilov YV et al. Unexpected Ring Opening During the Imination of Camphor-Type Bicyclic Ketones. European Journal of Organic Chemistry. 2021 Jan 22;2021(3):452-463. Epub 2020 Dec 27. doi: 10.1002/ejoc.202001397

Author

Chernyshov, Vladimir V. ; Yarovaya, Olga I. ; Vatsadze, Sergey Z. et al. / Unexpected Ring Opening During the Imination of Camphor-Type Bicyclic Ketones. In: European Journal of Organic Chemistry. 2021 ; Vol. 2021, No. 3. pp. 452-463.

BibTeX

@article{5d5501fd92034b2ab4959f739746ab10,
title = "Unexpected Ring Opening During the Imination of Camphor-Type Bicyclic Ketones",
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.",
keywords = "(−)-Fenchone, Benzimidazoles, Camphor, Monoterpenoids, Single-stage synthesis, AUXILIARY BASIS-SETS, NONNUCLEOSIDE INHIBITORS, BENZIMIDAZOLE DERIVATIVES, DOCKING, MEDIATED SYNTHESIS, BENZOXAZOLE, MOLECULES, BIOLOGICAL EVALUATION, HIV-1 REVERSE-TRANSCRIPTASE, ANTIFUNGAL, (&#8722, )-Fenchone",
author = "Chernyshov, {Vladimir V.} and Yarovaya, {Olga I.} and Vatsadze, {Sergey Z.} and Borisevich, {Sophia S.} and Trukhan, {Sergey N.} and Gatilov, {Yuri V.} and Peshkov, {Roman Yu} and Eltsov, {Ilia V.} and Martyanov, {Oleg N.} and Salakhutdinov, {Nariman F.}",
note = "Funding Information: The authors would like to express their gratitude to the Collective Use Chemical Service Center of the Siberian Branch of Russian Academy of Sciences for the obtained spectra and analytical data, as well as Dr. A.A. Nefedov (N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS) for the study of enantiomeric purity of reaction mixtures. All calculations were carried out on a cluster computer in the regional centre for shared computer equipment at the Ufa Institute of Chemistry UFRC RAS. The reported study was funded by RFBR, project number 19‐33‐90080. Publisher Copyright: {\textcopyright} 2020 Wiley-VCH GmbH Copyright: Copyright 2020 Elsevier B.V., All rights reserved.",
year = "2021",
month = jan,
day = "22",
doi = "10.1002/ejoc.202001397",
language = "English",
volume = "2021",
pages = "452--463",
journal = "European Journal of Organic Chemistry",
issn = "1434-193X",
publisher = "Wiley-Blackwell",
number = "3",

}

RIS

TY - JOUR

T1 - Unexpected Ring Opening During the Imination of Camphor-Type Bicyclic Ketones

AU - Chernyshov, Vladimir V.

AU - Yarovaya, Olga I.

AU - Vatsadze, Sergey Z.

AU - Borisevich, Sophia S.

AU - Trukhan, Sergey N.

AU - Gatilov, Yuri V.

AU - Peshkov, Roman Yu

AU - Eltsov, Ilia V.

AU - Martyanov, Oleg N.

AU - Salakhutdinov, Nariman F.

N1 - Funding Information: The authors would like to express their gratitude to the Collective Use Chemical Service Center of the Siberian Branch of Russian Academy of Sciences for the obtained spectra and analytical data, as well as Dr. A.A. Nefedov (N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS) for the study of enantiomeric purity of reaction mixtures. All calculations were carried out on a cluster computer in the regional centre for shared computer equipment at the Ufa Institute of Chemistry UFRC RAS. The reported study was funded by RFBR, project number 19‐33‐90080. Publisher Copyright: © 2020 Wiley-VCH GmbH Copyright: Copyright 2020 Elsevier B.V., All rights reserved.

PY - 2021/1/22

Y1 - 2021/1/22

N2 - 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.

AB - 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.

KW - (−)-Fenchone

KW - Benzimidazoles

KW - Camphor

KW - Monoterpenoids

KW - Single-stage synthesis

KW - AUXILIARY BASIS-SETS

KW - NONNUCLEOSIDE INHIBITORS

KW - BENZIMIDAZOLE DERIVATIVES

KW - DOCKING

KW - MEDIATED SYNTHESIS

KW - BENZOXAZOLE

KW - MOLECULES

KW - BIOLOGICAL EVALUATION

KW - HIV-1 REVERSE-TRANSCRIPTASE

KW - ANTIFUNGAL

KW - (&#8722

KW - )-Fenchone

UR - http://www.scopus.com/inward/record.url?scp=85097617232&partnerID=8YFLogxK

U2 - 10.1002/ejoc.202001397

DO - 10.1002/ejoc.202001397

M3 - Article

AN - SCOPUS:85097617232

VL - 2021

SP - 452

EP - 463

JO - European Journal of Organic Chemistry

JF - European Journal of Organic Chemistry

SN - 1434-193X

IS - 3

ER -

ID: 27063915