INVESTIGATION OF PHENANTHRIDONE AND DIOXOTETRAHYDRODIAZAPYRENE. 4. SYNTHESIS OF AMINO-SUBSTITUTED PHENANTHRIDONES and DIOXOTETRAHYDRODIAZAPYRENES

Article abstract of DOI:10.1007/BF00505997

The corresponding mono-, di-, and triamino derivatives substituted in the 2, 4, and 8 positions of the phenanthridone ring were obtained by reduction of mono-, di-, and trinitro-substituted phenanthridone (I), phenanthridone-10-carboxylic acid (II), phenanthridone-1-carboxylic acid (III), 4H-cyclopentaphenanthridine-5,9-dione (IV), 4H-cyclopentaphenanthridin-5-one (V), 5,10-dioxo-4,5,9,10-tetrahydro-4,9-diazapyrene(VI), and 5,9-dioxo-4,5,9,10-tetrahydro-4,10-diazapyrene (VII) with powdered iron in an electrolyte medium, with hydrogen in the presence of a nickel catalyst, or with stannous chloride.The 2,4,7,9-tetraamino derivative of VI was similarly obtained. 1-Amino, 7-amino-, and 10-aminophenanthridones were obtained by the Schmidt reaction from the corresponding carboxylic acids. 1,10-Diamino- and 3,8-diaminophenanthridones were similarly obtained from the corresponding aminofluorenones.