133671-46-2Relevant academic research and scientific papers
Amination by lithium alkylamide reagents of ketimines derived from 2-(trifluoromethyl)anilines and methyl halophenyl ketones and their cyclization products 2-(halophenyl)quinolin-4-amines
Strekowski, Lucjan,Janda, Lubomir,Patterson, Steven E.,Nguyen, Johnny
, p. 3273 - 3282 (2007/10/03)
The title ketimines containing a fluorine atom at position 2 of the phenyl group are efficiently cyclized under mild conditions to N-[2-(dimethylamino)ethyl]-2-(2-fluorophenyl)quinolin-4-amines by the reaction with a lithium reagent derived from N,N-dimethylethylenediamine. The facile regioselective displacement of C2-F in the presence of another fluorine atom at the phenyl group by the same reagent or N-lithio-N'-methylpiperazide at a higher temperature is explained in terms of a complex induced proximity effect (CIPE) process. The CIPE process is operative in amination of the 2-fluoro-phenyl ketimines by the more reactive piperazide reagent prior cyclization to quinolines. The 2-chloro-phenyl derivatives are much less reactive in the CIPE assisted amination.
Synthesis and quantitative structure-activity relationship analysis of 2-(aryl or heteroaryl)quinolin-4-amines, a new class of anti-HIV-1 agents
Strekowski,Mokrosz,Honkan,Czarny,Cegla,Wydra,Patterson,Schinazi
, p. 1739 - 1746 (2007/10/02)
Thirty-eight 2-(aryl or heteroaryl)quinolin-4-amines, N,N-disubstituted, N-monosubstituted, and without a substituent at the amino group have been synthesized with use of novel chemistries developed by us recently. Some of these derivatives show anti-HIV-
