Perilithiation and the synthesis of 8-substituted-1-naphthamides

Article abstract of DOI:10.1016/S0040-4020(99)00881-9

Attempted perilithiation of 1-naphthamides with their 2-positions blocked leads only to nucleophilic attack on the aromatic ring, but perilithiation of naphthalenes bearing 1-substituents such as -NMe₂ or CH₂NMe₂ allows the synthesis of 8-substituted-1-naphthamldes. The 8- CH₂NMe₂ substituents can be converted to carbonyl groups by Polonovski reactions; other 8-substituents may be introduced by using naphthalic anhydride as a starting material.