Direct, efficient syntheses of the benzimidazo [2, 1-a] isoquinoline ring system have been achieved with 2-bromoarylaldehydes, terminal alkynes, and 1, 2-phenylenediamines by a microwave-accelerated tandem process in which a Sonogashira coupling, 5-endo cyclization, oxidative aromatization, and 6-endo cyclization can be performed in a single synthetic operation.