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

J Clayden, CS Frampton, C McCarthy, N Westlund

Index: Clayden, Jonathan; Frampton, Christopher S.; McCarthy, Catherine; Westlund, Neil Tetrahedron, 1999 , vol. 55, # 49 p. 14161 - 14184

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Citation Number: 52

Abstract

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- naphthamides. The 8-CH2NMe2 substituents can be converted to carbonyl groups by Polonovski reactions; other 8-substituents may be introduced by using naphthalic ...