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

✍ Scribed by Necdet Coşkun

• Book ID: 104209008
• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 433 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)01046-1

✦ Synopsis

N-Arylphenacyiamine oximes 1 reacted with aryl isocyanates in refluxing benzene to give bis(arylcarbamoyi)-N-arylphenacylamine oximes 2 in good yields. Compounds 2 reacted with equimolar amount of TsOH.l-hO in THF at room temperature to give imidazol-2-ones 5 and Oarylcarbamoylhydroxylammonium tosylates 6 in high yields. Compounds 2 were heated under vacuum to induce Bzckmann fragmentation but the resulting products were 1,3,4-triaryl-i,3-dihydroimidazol-2-ones 5 instead of the expected i,3-diazetidinones 4.