A convenient synthesis of 1H-pyrrolo(3,2-c)quinoline-6,9-diones and 11H-indolo(3,2-c)quinoline-1,4-diones derivatives.

Abstract

8-Methoxy-2,3,4-trimethyl-1H-pyrrolo[3,2-c]quinoline-6,9-dione (28) and 2-methoxy-6-methyl-7,8,9,10-tetrahydro-11H-indolo[3,2-c]quinoline-1,4-dione (31) can be obtained from 4-hydrazino-6-methoxy-2-methyl-5-quinolinamine (21). The synthetic method consists increating the pyrrole or indole nucleus by applying Fischer''s indole synthesis to the hydrazones (22 and 24) to give the amines (23 and 25, respectively). The catalytic dehydrogenation of 25 leads to the quinolinamine (26). The oxidation of the amines (23, 25 and 26) by Fremy''s reagent (potassium nitrosodisulfonate) gives the quinones (28, 31 and 35). The nucleophilic substitution of the methoxy group by aziridine leads to 29, 33 and 36, which have moderate cytotoxic activity on L 1210 cells.