Synthesis of polyfluorinated aminoquinolines via nitroquinolines

Synthesis of polyfluorinated aminoquinolines via nitroquinolines Full article

Journal

Journal of Fluorine Chemistry
ISSN: 0022-1139

Output data

Year: 2018, Volume: 211, Pages: 14-23 Pages count : 10 DOI: 10.1016/j.jfluchem.2018.04.006

Tags

Polyfluorinated quinolines; Nitration; Reduction of nitroquinolines; Polyfluorinated aminoquinolines

Authors

Skolyapova Alexandrina D. ¹ , Selivanova Galina A. ¹ , Tretyakov Evgeny V. ^1,2 , Bagryanskaya Irina Yu. ^1,2 , Shteingarts Vitalij D. ¹

Affiliations

1	(Данные Web of science) NN Vorozhtsov Inst Organ Chem, 9 Ac Lavrentiev Ave, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, 2 Pirogova Str, Novosibirsk 630090, Russia

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.

Skolyapova A.D. , Selivanova G.A. , Tretyakov E.V. , Bagryanskaya I.Y. , Shteingarts V.D.
Synthesis of polyfluorinated aminoquinolines via nitroquinolines
Journal of Fluorine Chemistry. 2018. V.211. P.14-23. DOI: 10.1016/j.jfluchem.2018.04.006 WOS Scopus РИНЦ

Published print:

Jul 1, 2018

Web of science	WOS:000435061600002
Scopus	2-s2.0-85045573898
Elibrary	35491374
OpenAlex	W2797186515