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Synthesis of polyfluorinated aminoquinolines via nitroquinolines. / Skolyapova, Alexandrina D.; Selivanova, Galina A.; Tretyakov, Evgeny V. et al.

In: Journal of Fluorine Chemistry, Vol. 211, 01.07.2018, p. 14-23.

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

Harvard

Skolyapova, AD, Selivanova, GA, Tretyakov, EV, Bagryanskaya, IY & Shteingarts, VD 2018, 'Synthesis of polyfluorinated aminoquinolines via nitroquinolines', Journal of Fluorine Chemistry, vol. 211, pp. 14-23. https://doi.org/10.1016/j.jfluchem.2018.04.006

APA

Skolyapova, A. D., Selivanova, G. A., Tretyakov, E. V., Bagryanskaya, I. Y., & Shteingarts, V. D. (2018). Synthesis of polyfluorinated aminoquinolines via nitroquinolines. Journal of Fluorine Chemistry, 211, 14-23. https://doi.org/10.1016/j.jfluchem.2018.04.006

Vancouver

Skolyapova AD, Selivanova GA, Tretyakov EV, Bagryanskaya IY, Shteingarts VD. Synthesis of polyfluorinated aminoquinolines via nitroquinolines. Journal of Fluorine Chemistry. 2018 Jul 1;211:14-23. doi: 10.1016/j.jfluchem.2018.04.006

Author

Skolyapova, Alexandrina D. ; Selivanova, Galina A. ; Tretyakov, Evgeny V. et al. / Synthesis of polyfluorinated aminoquinolines via nitroquinolines. In: Journal of Fluorine Chemistry. 2018 ; Vol. 211. pp. 14-23.

BibTeX

@article{8ed88ac11cdf4b7dbfcf775880d3e50d,
title = "Synthesis of polyfluorinated aminoquinolines via nitroquinolines",
abstract = "Transformation of 14 quinolines polyfluorinated in the benzene moiety was investigated in nitration systems: a mixture of HNO3 and H2SO4, NaNO3 in H2SO4, NO2BF3OH in sulfolane, or NaNO3 in oleum. 5-Nitro- and/or 8-nitro derivatives formed if positions 5 or 8 were unoccupied in the starting compounds. Otherwise, nitro products were not detectable, and the initial compounds were oxidized. In some cases, F atoms at the ortho position relative to the nitro group were substituted thus affording hydroxynitroquinolines. Polyfluorinated 2-chloroquinolines were nitrated more easily than were quinolines not containing a substituent at position 2. Thus, a method is proposed for reduction of nitroquinolines to aminoquinolines that are not available via other approaches.",
keywords = "Nitration, Polyfluorinated aminoquinolines, Polyfluorinated quinolines, Reduction of nitroquinolines",
author = "Skolyapova, {Alexandrina D.} and Selivanova, {Galina A.} and Tretyakov, {Evgeny V.} and Bagryanskaya, {Irina Yu} and Shteingarts, {Vitalij D.}",
note = "Publisher Copyright: {\textcopyright} 2018 Elsevier B.V.",
year = "2018",
month = jul,
day = "1",
doi = "10.1016/j.jfluchem.2018.04.006",
language = "English",
volume = "211",
pages = "14--23",
journal = "Journal of Fluorine Chemistry",
issn = "0022-1139",
publisher = "Elsevier",

}

RIS

TY - JOUR

T1 - Synthesis of polyfluorinated aminoquinolines via nitroquinolines

AU - Skolyapova, Alexandrina D.

AU - Selivanova, Galina A.

AU - Tretyakov, Evgeny V.

AU - Bagryanskaya, Irina Yu

AU - Shteingarts, Vitalij D.

N1 - Publisher Copyright: © 2018 Elsevier B.V.

PY - 2018/7/1

Y1 - 2018/7/1

N2 - Transformation of 14 quinolines polyfluorinated in the benzene moiety was investigated in nitration systems: a mixture of HNO3 and H2SO4, NaNO3 in H2SO4, NO2BF3OH in sulfolane, or NaNO3 in oleum. 5-Nitro- and/or 8-nitro derivatives formed if positions 5 or 8 were unoccupied in the starting compounds. Otherwise, nitro products were not detectable, and the initial compounds were oxidized. In some cases, F atoms at the ortho position relative to the nitro group were substituted thus affording hydroxynitroquinolines. Polyfluorinated 2-chloroquinolines were nitrated more easily than were quinolines not containing a substituent at position 2. Thus, a method is proposed for reduction of nitroquinolines to aminoquinolines that are not available via other approaches.

AB - Transformation of 14 quinolines polyfluorinated in the benzene moiety was investigated in nitration systems: a mixture of HNO3 and H2SO4, NaNO3 in H2SO4, NO2BF3OH in sulfolane, or NaNO3 in oleum. 5-Nitro- and/or 8-nitro derivatives formed if positions 5 or 8 were unoccupied in the starting compounds. Otherwise, nitro products were not detectable, and the initial compounds were oxidized. In some cases, F atoms at the ortho position relative to the nitro group were substituted thus affording hydroxynitroquinolines. Polyfluorinated 2-chloroquinolines were nitrated more easily than were quinolines not containing a substituent at position 2. Thus, a method is proposed for reduction of nitroquinolines to aminoquinolines that are not available via other approaches.

KW - Nitration

KW - Polyfluorinated aminoquinolines

KW - Polyfluorinated quinolines

KW - Reduction of nitroquinolines

UR - http://www.scopus.com/inward/record.url?scp=85045573898&partnerID=8YFLogxK

U2 - 10.1016/j.jfluchem.2018.04.006

DO - 10.1016/j.jfluchem.2018.04.006

M3 - Article

AN - SCOPUS:85045573898

VL - 211

SP - 14

EP - 23

JO - Journal of Fluorine Chemistry

JF - Journal of Fluorine Chemistry

SN - 0022-1139

ER -

ID: 12668197