A FORMAL NEW ACCESS TO THE BENZO[C]PHENANTHRIDINE ALKALOIDS, SYNTHESIS OF NITIDINE AND O-METHYL FAGARONINE ANALOGS

Previously unreported 2-aryl-1-naphthylamines were obtained in good yields from 2 aryl-1-tetraloneoximes by using the Semmler-Wolf reaction but omitting the acetic anhydride usually present in the reaction mixture. From these amines, through the thermal cyclization of their corresponding ethyl carbamates, a new access to the benzo[c]phenanthridin-6(5H)-ones was found. Preparation of water-soluble Nitidine and O-Methyl Fagaronine analogues bearing an alkylamino side chain on the C-6 position was achieved from these compounds.