Tetrahedron p. 14161 - 14184 (1999)
Update date:2022-08-05
Topics:
Clayden, Jonathan
Frampton, Christopher S.
McCarthy, Catherine
Westlund, Neil
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.
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