Domino reactions of vinyl ethynyl ketones with 1-aryl-3,4-dihydroisoquinolines — Search for selectivity

We report an efficient domino reaction for synthesizing new pyrrolo[2,1-a]isoquinolines from 1-aryl-3,4-dihydroisoquinolines and vinyl ethynyl ketones. We also address the chemical selectivity of vinyl ethynyl ketones; i.e., adduct formation by the double or triple bond. The reaction outcome depends on the solvent, temperature, microwave irradiation, and catalyst. Donor substituents in the initial isoquinolines provide a regioselective addition to double or triple bonds. © 2018 Elsevier B.V.