Reactivity of bis(arylcarbamoyl)-N-arylphenacylamine oximes. Synthesis of 1,3-dihydroimidazol-2-ones and N-unsubstituted O-arylcarbamoylhydroxylamines

Coskun N.

TETRAHEDRON, vol.55, no.2, pp.475-484, 1999 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 55 Issue: 2
  • Publication Date: 1999
  • Doi Number: 10.1016/s0040-4020(98)01046-1
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.475-484
  • Bursa Uludag University Affiliated: Yes


N-Arylphenacylamine oximes I reacted with aryl isocyanates in refluxing benzene to give bis(arylcarbamoyl)-N-arylphenacylamine oximes 2 in good yields. Compounds 2 reacted with equimolar amount of TsOH.H2O in THF at room temperature to give imidazol-2-ones 5 and O-arylcarbamoylhydroxylammonium tosylates 6 in high yields. Compounds 2 were heated under vacuum to induce Beckmann fragmentation but the resulting products were 1,3,4-triaryl-1,3-dihydroimidazol-2-ones 5 instead of the expected 1,3-diazetidinones 4. (C) 1998 Elsevier Science Ltd. All rights reserved.