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

Attempted perilithiation of 1-naphthamides with their 2-positions blocked l eads only to nucleophilic attack on the aromatic ring, but perilithiation o f naphthalenes bearing l-substituents such as -NMe2 or -CH2NMe2 allows the synthesis of 8-substituted-1-naphthamides. The 8-CH2NMe2 substituents can b e converted to carbonyl groups by Polonovski reactions; other 8-substituent s may be introduced by using naphthalic anhydride as a starting material. ( C) 1999 Published by Elsevier Science Ltd. All rights reserved.