Synthesis of dimethyl 1,2-dihydroisoquinolines through the reaction of isoquinoline and dimethyl acetylenedicarboxylate in the presence of amides

Isoquinoline reacts smoothly with dimethyl acetylenedicarboxylate (DMAD) in the presence of amides to produce dimethyl 2-[1-[aryl(alkyl)carbonylamino]-2(1H)-isoquinolinyl]-2-butenedioates. Reaction of quinoline with DMAD in the presence of benzamide led to dimethyl 2-[1-[(phenylcarbonyl)amino]-2(1H)-quinolinyl]-2-butenedioate.