Abstract Azomethine ylides generated from 5-(alkoxycarbonylmethyl) phenanthridinium cations were studied in 1, 3-dipolar cycloadditions with dimethyl maleate and dimethyl fumarate as dipolarophiles. The cycloadducts with the pyrrolidino [1, 2-f] phenanthridine skeleton easily underwent dehydrogenation. The structure of products was determined by X- ray, NMR and MS.