Interaction of quinolines polyfluorinated on the benzene moiety with sodium and potassium amides in liquid ammonia

被引：5

作者：

Gurskaya, Larisa Yu. ^{[1
]}

Selivanova, Galina A. ^{[1
]}

Shteingarts, Vitalij D. ^{[1
]}

机构：

[1] Russian Acad Sci, Siberian Branch, NN Vorozhtsov Novosibirsk Inst Organ Chem, Novosibirsk 630090, Russia

来源：

JOURNAL OF FLUORINE CHEMISTRY | 2012年 / 136卷

关键词：

Polyfluorinated quinolines; Methylquinolines; Aminoquinolines; Potassium (sodium) amide; Deprotonation; Polyfluorinated quinolinyl anions; Oxidative dehydroamination; NUCLEOPHILIC-SUBSTITUTION; MAGNETIC-RESONANCE; AMINO GROUP; HYDROGEN; FLUOROQUINOLINES; MUTAGENICITY; DERIVATIVES; RECEPTOR; ALKALI; RING;

D O I：

10.1016/j.jfluchem.2012.01.007

中图分类号：

O61 [无机化学];

学科分类号：

070301 ; 081704 ;

摘要：

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.

引用

页码：32 / 37

页数：6

共 34 条

[1]

Banks R.E., 1994, ORGANOFLUORINE CHEM, P638

[2] Lithiation of functionalized fluoroquinolines:: Synthesis of dihalo-2-phenylquinoline-4-carboxamides and in vitro evaluation as NK-3 receptor ligands for medical imaging studies [J].