BENZOTRIAZOLE STABILIZED LITHIUM INTERMEDIATES AS A ROUTE TO THE ELABORATION OF N-SUBSTITUENTS IN AMIDES

Lithiation of N-(benzotriazol-1-ylmethyl)benzamide or -(benzotriazol-1 -ylmethyl)-2,2-dimethylbutyramide, readily prepared from the correspon ding amides, formaldehyde and benzotriazole, followed by quenching wit h various electrophiles, such as alkyl halides, ketones or ester, give s the corresponding N-substituted derivatives. Subsequent displacement of the benzotriazole group with Grignard reagents, thiols or alcohols provides access to a wide variety of N-substituted amides in good yie lds. Treatment of the N-(benzotriazol-1-ylalkyl)benzamides with n-BuLi afforded the 1,1-dibenzamidoalkanes.