Nucleophilic Attack at Heterocyclic Nitrogen: Unusual Reactivity of the Benzotriazole Heterocyclic Ring

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Abstract

Grignard reagents attack 1-imidoylbenzotriazoles at the imidoyl carbon atom and also at the benzotriazolyl N-2 and N-3 atoms leading to complex reaction mixtures, the composition of which allowed identification of the main reaction paths. Mechanisms are discussed. Previous examples of nucleophilic attack on pyridine-like nitrogen atoms are reviewed. The 1-imidoylbenzotriazoles were prepared from amides with benzotriazole and phosphoryl chloride. Amides derived from secondary amines give α-(benzotriazol-1-yl) enamines.

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