Synthesis of H-Pyrazolo[5,1-a]isoquinolines via Silver(I)-Catalyzed Tandem Reaction of N′-(2-Alkynylbenzylidene)hydrazides with Propargyl Amine Derivatives

Abstract

We have developed a tandem reaction of N′-(2-alkynylbenzylidene)hydrazides with propargyl amine derivatives catalyzed by silver triflate to provide 2-(aminomethyl)-H-pyrazolo[5,1-a]isoquinolines. This reaction proceeds through a tandem 6-endo-cyclization, nucleophilic addition, 5-endo-cyclization and aromatization, leading to the cycloadducts in moderate to good yields with exclusive regioselectivity.

Key words

N′-(2-alkynylbenzylidene)hydrazides - propargyl amine derivatives - silver triflate - tandem reactions - 1,3-dipolar cycloaddition reactions

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