Parallel solid-phase synthesis of disubstituted 3-(1H-benzo[d]imidazol-2-yl) imidazolIdiEe-2,4-dioees and 3-(1H-benzo[d]imidazol-2-yl)-2-thioxoimidazolidin-4-ones

摘要

A multistep approach to construct novel 3-(1H-benzo[d]imidazol-2-yl)imidazolidine-2,4-diones and 3-(1H-benzo[d]imidazol-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 aminobenzimid-azole provided following Fmoc elimination free amine. Treatment of the free amine with 1,1'-carbonyl-diimidazole or l,l'-thiocarbonyldiimidazole furnished the corresponding hydantoins and thiohydantoins via intramolecular cyclization. The desired aminobenzimidazole tethered hydantoins or thiohydantoins were isolated in good yields.