New synthesis of amines and amides mediated by additions of benzotriazole to enamines and enamides and transformations of the adducts

Abstract

Adducts of type N - C - Bt can be obtained in which the nitrogen atom is derived from an N-vinyl non-basic heterocyclic NH compound or a secondary amide, or in which the central carbon is derived from a ketone by the addition of benzotriazole to an enamine or enamide. Thus, 9-vinylcarbazole, 1-vinylpyrrolidin-2-one and 1-(1-ethylprop-1-enyl)pyrrolidine afforded the corresponding N-(1-benzotriazolylalkyl)-substituted compounds which could be alkylated by various methods in good yield. The range of benzotriazole mediated syntheses of amines and amides is significantly extended in this way.