Synthesis of [1,2,4]triazolo[3,4-a]isoquinolines and pyrrolo[2,1-a]isoquinolines using α-keto hydrazonoyl halides

Article abstract of DOI:10.1016/0040-4020(96)00024-5

Treatment of α-keto hydrazonoyl halides 1 with 3,4-dihydro-6,7-dimethoxyisoquinoline 3 and its 1-methyl derivative 4 in the presence of triethylamine in tetrahydrofuran at reflux afforded the corresponding cycloadducts 6 and 9, respectively. The same halides 1 react with 1-cyanomethyl-3,4-dihydro-6,7-dimethoxyisoquinoline 5 and afforded pyrrolo[2,1-a]isoquinoline derivatives 12 in high yield.