The regioselective synthesis of pyrazole triflones has been achieved by 1, 3-dipolar cycloaddition of triflyl alkynes and hydrazonoyl chloride in the presence of Hünig's base. Pyrazolo [5, 1-a] isoquinoline triflones were also regioselectively synthesized for the first time via tandem 1, 3-dipolar cycloaddition/oxidative aromatization between triflyl alkynes and C, N-cyclic azomethine imines.