Abstract
Abstract 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-fluorophenyl ketimines by the more reactive piperazide reagent prior cyclization to quinolines. The 2-chlorophenyl derivatives are much less reactive in the CIPE assisted amination.
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