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Bromination of quinolin-2(1H)-ones fluorinated on the benzene moiety. / Verkhov, Fyodor K.; Skolyapova, Alexandrina D.; Krasnov, Vyacheslav I. et al.

In: Journal of Fluorine Chemistry, Vol. 268, 110132, 05.2023.

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

Harvard

Verkhov, FK, Skolyapova, AD, Krasnov, VI, Bagryanskaya, IY, Andreev, RV, Karpova, EV, Kalizhnikova, EE & Selivanova, GA 2023, 'Bromination of quinolin-2(1H)-ones fluorinated on the benzene moiety', Journal of Fluorine Chemistry, vol. 268, 110132. https://doi.org/10.1016/j.jfluchem.2023.110132

APA

Verkhov, F. K., Skolyapova, A. D., Krasnov, V. I., Bagryanskaya, I. Y., Andreev, R. V., Karpova, E. V., Kalizhnikova, E. E., & Selivanova, G. A. (2023). Bromination of quinolin-2(1H)-ones fluorinated on the benzene moiety. Journal of Fluorine Chemistry, 268, [110132]. https://doi.org/10.1016/j.jfluchem.2023.110132

Vancouver

Verkhov FK, Skolyapova AD, Krasnov VI, Bagryanskaya IY, Andreev RV, Karpova EV et al. Bromination of quinolin-2(1H)-ones fluorinated on the benzene moiety. Journal of Fluorine Chemistry. 2023 May;268:110132. doi: 10.1016/j.jfluchem.2023.110132

Author

Verkhov, Fyodor K. ; Skolyapova, Alexandrina D. ; Krasnov, Vyacheslav I. et al. / Bromination of quinolin-2(1H)-ones fluorinated on the benzene moiety. In: Journal of Fluorine Chemistry. 2023 ; Vol. 268.

BibTeX

@article{d5a2ff78b3844e2891f1623541e44896,
title = "Bromination of quinolin-2(1H)-ones fluorinated on the benzene moiety",
abstract = "Bromination of ten known fluorinated quinolin-2(1H)-ones by the KBrO3/HBr system is investigated. If there is no F atom in the position 6 of substrate, the Br atom is introduced into position 3 or 6 to form monobromo derivative, the second Br atom is introduced into the same positions leading to 3,6-dibromo product. If a F atom is in position 6, the 3-bromo product is initially obtained, which gives a 3,5-dibromo or 3,8-dibromo derivatives upon further bromination depending on the F atoms positions. In this case, when both positions 5 and 8 of 3-bromoquinolin-2(1H)-one are unsubstituted, the second Br atom is introduced into position 8. If there are more than two F atoms in the benzene moiety, the sole 3-bromo product is obtained. Relative (ΔE) energies of the considered σ−complexes estimated by DFT calculations for the reactions in question are consistent with the experimentally observed regioselectivity.",
keywords = "Bromination, Bromofluoroquinolin-2-(1H)-ones, Fluorinated quinolin-2(1H)-ones",
author = "Verkhov, {Fyodor K.} and Skolyapova, {Alexandrina D.} and Krasnov, {Vyacheslav I.} and Bagryanskaya, {Irina Yu} and Andreev, {Rodion V.} and Karpova, {Elena V.} and Kalizhnikova, {Evgenya E.} and Selivanova, {Galina A.}",
note = "The authors thank the Multi-Access Chemical Service Center SB RAS for spectral and analytical measurements, and Ministry of Science and Higher Education of the Russian Federation (Project FWUE-2022-0002 ) for financial support. The authors thank Ludmila Filatova for conducting a literary search. Публикация для корректировки.",
year = "2023",
month = may,
doi = "10.1016/j.jfluchem.2023.110132",
language = "English",
volume = "268",
journal = "Journal of Fluorine Chemistry",
issn = "0022-1139",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Bromination of quinolin-2(1H)-ones fluorinated on the benzene moiety

AU - Verkhov, Fyodor K.

AU - Skolyapova, Alexandrina D.

AU - Krasnov, Vyacheslav I.

AU - Bagryanskaya, Irina Yu

AU - Andreev, Rodion V.

AU - Karpova, Elena V.

AU - Kalizhnikova, Evgenya E.

AU - Selivanova, Galina A.

N1 - The authors thank the Multi-Access Chemical Service Center SB RAS for spectral and analytical measurements, and Ministry of Science and Higher Education of the Russian Federation (Project FWUE-2022-0002 ) for financial support. The authors thank Ludmila Filatova for conducting a literary search. Публикация для корректировки.

PY - 2023/5

Y1 - 2023/5

N2 - Bromination of ten known fluorinated quinolin-2(1H)-ones by the KBrO3/HBr system is investigated. If there is no F atom in the position 6 of substrate, the Br atom is introduced into position 3 or 6 to form monobromo derivative, the second Br atom is introduced into the same positions leading to 3,6-dibromo product. If a F atom is in position 6, the 3-bromo product is initially obtained, which gives a 3,5-dibromo or 3,8-dibromo derivatives upon further bromination depending on the F atoms positions. In this case, when both positions 5 and 8 of 3-bromoquinolin-2(1H)-one are unsubstituted, the second Br atom is introduced into position 8. If there are more than two F atoms in the benzene moiety, the sole 3-bromo product is obtained. Relative (ΔE) energies of the considered σ−complexes estimated by DFT calculations for the reactions in question are consistent with the experimentally observed regioselectivity.

AB - Bromination of ten known fluorinated quinolin-2(1H)-ones by the KBrO3/HBr system is investigated. If there is no F atom in the position 6 of substrate, the Br atom is introduced into position 3 or 6 to form monobromo derivative, the second Br atom is introduced into the same positions leading to 3,6-dibromo product. If a F atom is in position 6, the 3-bromo product is initially obtained, which gives a 3,5-dibromo or 3,8-dibromo derivatives upon further bromination depending on the F atoms positions. In this case, when both positions 5 and 8 of 3-bromoquinolin-2(1H)-one are unsubstituted, the second Br atom is introduced into position 8. If there are more than two F atoms in the benzene moiety, the sole 3-bromo product is obtained. Relative (ΔE) energies of the considered σ−complexes estimated by DFT calculations for the reactions in question are consistent with the experimentally observed regioselectivity.

KW - Bromination

KW - Bromofluoroquinolin-2-(1H)-ones

KW - Fluorinated quinolin-2(1H)-ones

UR - https://www.scopus.com/record/display.uri?eid=2-s2.0-85152885941&origin=inward&txGid=6f28541c51de92ac3687490412c252bd

UR - https://www.mendeley.com/catalogue/5e1d50fc-7de7-3cf2-b7a4-68266086d6bb/

U2 - 10.1016/j.jfluchem.2023.110132

DO - 10.1016/j.jfluchem.2023.110132

M3 - Article

VL - 268

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

M1 - 110132

ER -

ID: 59646549