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

[摘要] 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.

[发布日期] 2011-12-28

[关键词] Solid phase synthesis;Benzimidazole;Amino acid;Hydantoin;Thiohydantoin;Heterocycles;Intramolecular cyclization