1,3-Dipolar cycloadditions of C,N-cyclic azomethine imines with γ-NHTs-α,β-unsaturated ketones were developed to synthesize tricyclic dinitrogen-fused heterocycles. Highly functionalized tricyclic tetrahydroisoquinolines were readily obtained in good to high yields in the [3 + 2]-cycloaddition reaction of N-Bz-protected C,N-cyclic azomethine imines with γ-NHTs-α,βunsaturated ketones under mild reaction conditions. Moreover, DABCO-catalyzed cycloaddition of N-Ts-protected C,N-cyclic azomethine imines with γ-NHTs-α,β-unsaturated ketones followed by cleavage of the tosyl group is a convenient route to synthesize tetrahydropyrazolo [5,1-a]isoquinolines in good yields with excellent diastereoselectivities.

An innovative and efficient approach has been developed for the synthesis of 5,6-dihydropyrazolo[5,1-a]isoquinolines. This one-pot tandem reaction involves the reaction of C,N-cyclic azomethine imines with α,β-unsaturated ketones, using K2CO3 as the base and DDQ as the oxidant. The process results in functionalized 5,6-dihydropyrazolo[5,1-a]isoquinolines with good yields. This convenient one-step method encompasses a tandem [3 + 2]-cycloaddition, detosylation, and oxidative aromatization.