Abstract
The three isomeric 2-, 3- and 4-pivalamidoquinolines react with lithiating reagents to give their metalation or nucleophilic addition products. Metalation occurs best with the 2-substituted isomer. Suprisingly 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.
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