Parallel solid-phase synthesis of disubstituted 3-(1H-benzo[d]imidazol-2-yl) imidazolidine-2,4-diones and 3-(1H-benzo[d]imidazol-2-yl)-2-thioxoimidazolidin-4-ones
Parallel solid-phase synthesis of disubstituted 3-(1H-benzo[d]imidazol-2-yl) imidazolidine-2,4-diones and 3-(1H-benzo[d]imidazol-2-yl)-2-thioxoimidazolidin-4-ones
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DOI：
10.1016/j.tetlet.2011.10.064
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发表时间：
2011-12-28
影响因子：
1.8
通讯作者：
Nefzi, Adel
中科院分区：
文献类型：
--
作者：
Dadiboyena, Sureshbabu;Nefzi, Adel
描述了从市售氨基酸、胺和羧酸构建新型 3-(1H-苯并咪唑-2-基)咪唑烷-2,4-二酮和 3-(1H-苯并咪唑-2-基)-2-硫代咪唑烷-4-酮的多步骤方法。 Fmoc-氨基酸与树脂结合的氨基苯并咪唑的偶联在Fmoc消除游离胺后提供。用1,1'-羰基二咪唑或1,1'-硫代羰基二咪唑处理游离胺，通过分子内环化提供相应的乙内酰脲和硫代乙内酰脲。以良好的收率分离出所需的氨基苯并咪唑系链乙内酰脲或硫代乙内酰脲。 (C) 2011 Elsevier Ltd. 保留所有权利。
A multistep approach to construct novel 3-(1H-benzoldlimidazol-2-yl)imidazolidine-2,4-diones and 3-(1H-benzordlimidazol-2-yl)-2-thioxoimidazolidin-4-ones from commercially available amino acids, amines, and carboxylic acids is described. Coupling of Fmoc-amino acid to resin-bound aminobenzimidazole provided following Fmoc elimination free amine. Treatment of the free amine with 1,1'-carbonyldiimidazole or 1,1'-thiocarbonyldiimidazole furnished the corresponding hydantoins and thiohydantoins via intramolecular cyclization. The desired aminobenzimidazole tethered hydantoins or thiohydantoins were isolated in good yields. (C) 2011 Elsevier Ltd. All rights reserved.