Condensed heterocyclic lactams. I. Study on the cyclization methods resulting in 4-aryl-3,4-dihydroquinolin-2(1H)-ones

Cyclization reactions with polyphosphoric acid of 3-aryl-3-hydroxypropionanilides carrying a p-nitro- 7a or p-amino substituent 10 on the C-3 phenyl group were investigated. In the case of p-nitro substitution the preferred reaction is, instead of cyclization, the elimination of water to give the corresponding cinnamic acid derivative. On the other hand, reaction of the p-amino-substituted analogue gave the new compound 4-(4-aminophenyl)-3,4-dihydroquinolin-2(1H)-one ( 2b ) in a good yield. The intermediate product of the cyclization was isolated and its structure established.