1020846-60-9Relevant academic research and scientific papers
New approaches to the synthesis of 4-(2-aminophenyl)-1,3-dihydro-2H- imidazol-2-ones and 3-ureidoindoles and a study of their interconversion
Klasek, Antonin,Lycka, Antonin,Holcapek, Michal,Hoza, Ignac
experimental part, p. 354 - 370 (2009/02/07)
3-Alkyl/aryl-3-ureido-1H,3H-quinoline-2,4-diones (2) and 3a-alkyl/aryl-9b-hydroxy-3,3a,5,9b-tetrahydro-1H-imidazo[4,5-c]quinoline-2, 4-diones (3) react in boiling concentrated HCl to give 5-alkyl/aryl-4-(2- aminophenyl)-1,3-dihydro-2H-imidazol-2-ones (6). The same compounds were prepared by the same procedure from 2-alkyl/aryl-3-ureido-1H-indoles (4), which were obtained from the reaction of 3-alkyl/aryl-3-aminoquinoline-2,4(1H,3H)- diones (1) with 1,3-diphenylurea or by the transformation of 3a-alkyl/aryl-9b-hydroxy-3,3a,5,9b-tetrahydro-1H-imidazo[4,5-c]quinoline-2, 4-diones (3) and 5-alkyl/aryl-4-(2-aminophenyl)-1,3-dihydro-2H-imidazol-2-ones (6) in boiling AcOH. The latter were converted into 1,3-bis[2-(2-oxo-2,3- dihydro-1H-imidazol-4-yl)phenyl]ureas (5) by treatment with triphosgene. All compounds were characterized by 1H- and 13C-NMR and IR spectroscopy, as well as atmospheric pressure chemical-ionisation mass spectra.
