Abstract: A primary functionalization of quinolines polyfluorinated at the benzene ring (5,7-difluoro-, 5,7,8-trifluoro-, 5,6,8-trifluoro-, 8-chloro-5,7-difluoro-, 5,6,7,8-tetrafluoro-, and 5,7,8-trifluoro-6-(trifluoromethyl)quinolines) by the reaction with nitrogen-centered nucleophiles (aqueous and liquid ammonia, hydrazine hydrate, piperidine) has been studied. If the molecule of fluorinated quinoline contains three or four halogen atoms, their combined orientation effect outweighs the influence of the heterocycle N atom. It was found that the orientation of substitution in the reactions of 5,6,8-trifluoro- and 5,7,8-trifluoro-6-(trifluoromethyl)quinolines with piperidine depends on temperature, because the enthalpy control of the ratio of the rates of competing reactions changes to the entropy control. Nineteen new quinoline derivatives containing F atoms and amino or modified amino groups in the benzene ring have been obtained.

Cite: Safina L.Y. , Selivanova G.A. , Bagryanskaya I.Y. , Shteingarts V.D.
Reaction of quinolines fluorinated at the benzene ring with nitrogen-centered nucleophiles
Russian Chemical Bulletin. 2009. V.58. N5. P.1049-1061. DOI: 10.1007/s11172-009-0134-z WOS Scopus РИНЦ

Dates:

Published print:	May 1, 2009
Published online:	Apr 17, 2010

Identifiers:

Web of science	WOS:000276772100025
Scopus	2-s2.0-77955729938
Elibrary	15312996
OpenAlex	W2062280255

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