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

被引:8
作者
Coskun, N [1 ]
机构
[1] Uludag Univ, Dept Chem, TR-16059 Bursa, Turkey
关键词
D O I
10.1016/S0040-4020(98)01046-1
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
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.
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页码:475 / 484
页数:10
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