Ringschlussreaktionen von 1-(2-Aminophenyl)-1-phenyl-äthylenen durch Kondensation mit Phosgen

Cyclization of 1-(2-aminophenyl)-1-phenyl-ethylenes or 1-(2-aminophenyl)-1-phenyl-propenes (II) by condensation with phosgene led to 4-phenyl-carbostyrils (III) or 2-chloro-4-phenyl-quinolines (IV). Similarly, thiophosgene afforded 4-phenyl-thiocarbostyril. Treatment of 1-(2-aminophenyl)-2-methyl-1-p-tolyl-propene (VII) with phosgene led to the corresponding isocyanate IX, which cyclized in the presence of aluminum chloride with loss of a methyl group to 3-methyl-4-p-tolyl-carbostyril (III-6). However, 1-(2-aminophenyl)-2-methyl-1-phenyl-propene (VIII) treated with phosgene gave the isocyanate XI and 3-phenyl-3-isopropenyloxindole (X). Cyclization of the isocyanate XI with aluminium chloride led simultaneously to 3-methyl-4-phenyl-carbostyril (XIV), and with migration of a methyl group to 3-methylene-4-methyl-4-phenyl-3. 4-dihydro-carbostyril (XV).