Abstract 8-Chloroberberine (V), obtained by treatment of oxyber-berine (I) with phosphorus oxychloride, is a reactive intermediate. Treatment with ammonia, methylamine, n- propylamine, aniline, and p-toluidine furnished the 8-berberinylidene derivatives IV and VII- X. Reaction of V with malononitrile, ethyl acetoacetate, and ethyl malonate anions yielded the 8-berberinylidene derivatives XII-XIV. Acid hydrolysis of XIV gave 8-berberinylacetic ...