ANNULATION REACTIONS OF 3-AMINIOSOQUINOLIN-1(2H)-ONE - SYNTHESIS OF PYRIMIDO[1,2-B]ISOQUINOLINES, PYRIDO-[2,3-C]ISOQUINOLINES AND PYRROLO[2,3-C]ISOQUINOLINES

Reactions of the title compound with the malonic acid derivatives diet hyl ethoxymethylenemalonate (EMME), ethyl ethoxymethylenecyanoacetate (EMCA) and ethoxymethylenemalononitrile (EMMN) are reported. Condensat ions occur at the amino group or C-4, depending on conditions and the former intermediate was successfully cyclized to the pyrimido[1,2-b]is oquinoline system. Reactions with 2,4-pentanedione and p-bromophenacyl bromide gave only the angular systems, pyrido[2,3-c]isoquinoline and pyrrolo[2,3-c]isoquinoline, respectively.