Three distinct reactions of 3,4-dihydroisoquinolines with azlactones: Novel synthesis of imidazoloisoquinolin-3-ones, benzo[a]quinolizin-4-ones, and benzo[d]azocin-4-ones

Rattana WorayuthakarnNopporn ThasanaSomsak RuchirawatChulabhorn Research InstituteMahidol UniversityThe Institute of Science and Technology for Research and Development, Mahidol University2018-08-202018-08-202006-12-07Organic Letters. Vol.8, No.25 (2006), 5845-5848152370602-s2.0-33846272750https://repository.li.mahidol.ac.th/handle/20.500.14594/22933(Diagram presented) A facile and direct synthetic entry to tricyclic imidazoloisoquinolin-3-ones and benzo[a]quinolizin-4-ones is reported based on the ring annulation of 1-unsubstituted and 1-substituted dihydroisoquinolines with azlactones under neutral conditions in a one-step procedure. Bicyclic 2,3-dihydrobenzo[djazocin-4-ones were also prepared using simple azlactone and 1-substituted dihydroisoquinolines in a one-pot reaction. © 2006 American Chemical Society.Mahidol UniversityBiochemistry, Genetics and Molecular BiologyChemistryThree distinct reactions of 3,4-dihydroisoquinolines with azlactones: Novel synthesis of imidazoloisoquinolin-3-ones, benzo[a]quinolizin-4-ones, and benzo[d]azocin-4-onesArticleSCOPUS10.1021/ol062429m