Abstract: The interaction of 5,6,7,8-tetrafluoro- (1) and 5,7,8-trifluoro-6-(trifluoromethyl)quinoline (2) with sodium or potassium amide in liquid ammonia proceeds as a nucleophile (NH2-) addition on the 2-position of the pyridine ring, the respective adducts being oxidized to give the respective quinoline-2-amines. In the case of 1 the amide addition is concurrent with aminodefluorination on the 6- and 7-positions. 5,6,8- (3). 5,7,8-trifluoro- (4) and 5,7-difluoroquinolines (5) with one amide equivalent undergo deprotonation of the C-H bond flanked by two ortho-fluorine atoms to produce the respective long-lived quinolinyl anions, which can be used as nucleophilic synthons as exemplified by their methylation to yield respective 6- and 7-methylpolyfluoroquinolines. With an excess of potassium amide the originally generated quinolinyl anions add an amide anion on the 2- or 4-position. (C) 2012 Elsevier B.V. All rights reserved.

Cite: Gurskaya L.Y. , Selivanova G.A. , Shteingarts V.D.
Interaction of quinolines polyfluorinated on the benzene moiety with sodium and potassium amides in liquid ammonia
Journal of Fluorine Chemistry. 2012. V.136. P.32-37. DOI: 10.1016/j.jfluchem.2012.01.007 WOS Scopus РИНЦ

Dates:

Published print:

Apr 1, 2012

Identifiers:

Web of science	WOS:000302976900006
Scopus	2-s2.0-84858444211
Elibrary	17980528
OpenAlex	W2076052281

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