Etude de la metallation des pivalamido-2, -3 et -4 quinoleines

Article abstract of DOI:10.1016/0022-328X(88)80652-1

The three isomeric 2-, 3- and 4-pivalamidoquinolines react with lithiating reagents to give either metalation or nucleophilic addition products.Metalation occurs best with the 2-substituted isomer.Surprisingly the 4-pivalamidoquinoline is lithiated at C(8).A new directing group derived from the amine, the ureido substituent, directs the lithiation at C(2) of the 3-aminoquinoline derivative.