1,3,4,5-Tetrahydrobenz[cd]indoles and related compounds. Part V. Some reactions of 1,2,4,5-tetrahydropyrrolo[3,2,1-ij]quinolin-6-one

Abstract

Bromination, dehydrogenation, the Mannich reaction, the Cope–Knoevenagel reaction, and the Schmidt reaction of 1,2,4,5-tetrahydropyrrolo[3,2,1-ij]quinolin-6-one are described. The oxime derived from this ketone forms a p-tolylsulphonyl derivative, which under Neber reaction conditions (sodium ethoxide in benzene) yields the expected keto-amine hydrochloride. The latter has been converted into the corresponding keto-urethane, which has been subjected to dehydrogenation, hydrogenolysis, and reduction with both potassium borohydride and lithium aluminium hydride.