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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

  作者 Klasek, A; Lycka, A; Holcapek, M; Hoza, I  
  选自 期刊  Helvetica Chimica Acta;  卷期  2008年91-2;  页码  354-370  
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[摘要]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/aryt-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 H-1-and C-13-NMR and IR spectroscopy, as welt as atmospheric pressure chemical-ionisation mass spectra.

 
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