Synthesis of novel fluorinated 4-aminoquinoline derivatives

New 4-aminoquinolines having a -CF2CH-(heteroaryl)-OH moiety are obtained in moderate yields from the electrochemical catalyzed reaction of the corresponding 4-amino-3-chlorodifluoroacetyl-2-methoxyquinoline in the presence of heteroaryl aldehydes. A one-pot intramolecular zinc mediated aromatic nucleophilic substitution also gave access to novel difluorinated 5-aminodihydropyrano[2,3-b]quinolin-4-ones.