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

TETRAHEDRON LETTERS

卷:52

Article

Dadiboyena, Sureshbabu¹  Nefzi, Adel^1,2 

[1] Torrey Pines Inst Mol Studies, Port St Lucie, FL 34987 USA

[2] Florida Atlantic Univ, Boca Raton, FL 33431 USA

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

DOI  :  10.1016/j.tetlet.2011.10.064

来源: Elsevier

【 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.

【 授权许可】

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