Steric factors in amide-directed metalations of N, N-dialkyl-6-methoxynaphthalene-2-carboxamides: synthesis of a sterically perturbed acylnaphthol

RD Bindal, JA Katzenellenbogen

文献索引：Bindal, Rajeshwar D.; Katzenellenbogen, John A. Journal of Organic Chemistry, 1987 , vol. 52, # 15 p. 3181 - 3185

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被引用次数: 17

摘要

The powerful ortho-metalating directive effect of the N, N-dialkylcarboxamide group can be used for the preparation of C-1 alkyl-substituted 2, 6-acylnaphthols. The alternative reaction pathways of C-1 metalation vs. acylation (carbonyl addition) in the reaction of alkyllithium reagents with Nfl-dialkyl-6-methoxynaphthalenecarboxamides depends upon the cumulative steric nature of the N-alkyl and lithium alkyl groups: The NJV-dimethylamide 7 ...