title: Synthesis of a Small Library of Imidazolidin-2-ones using Gold Catalysis on Solid Phase.
abstract: An efficient and high-yielding solid phase synthesis of a small library of imidazolidin-2-ones and imidazol-2-ones was carried out employing a high chemo- and regioselective gold-catalyzed cycloisomerization as a key step. Polymer-supported amino acids derivatized with several alkyne functionalities combined with tosyl- and phenylureas have been subjected to gold-catalysis exhibiting exclusively C-N bond formation. The present work proves the potential of solid phase synthesis and homogeneous gold catalysis as an efficient and powerful synthetic tool for the generation of drug-like heterocycles.
authors.affiliation: Department of Organic Chemistry, Faculty of Science, Institute of Molecular and Translational Medicine, Palacky University , 771 46 Olomouc, Czech Republic.|Instituto de Química Rosario-IQUIR (CONICET), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario , Suipacha 531, Rosario S2002LRK, Argentina.
authors.forename: Agustina
authors.initials: A
authors.lastname: La-Venia
authors.affiliation: Instituto de Química Rosario-IQUIR (CONICET), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario , Suipacha 531, Rosario S2002LRK, Argentina.
authors.forename: Noelia S
authors.initials: NS
authors.lastname: Medran
authors.affiliation: Department of Organic Chemistry, Faculty of Science, Institute of Molecular and Translational Medicine, Palacky University , 771 46 Olomouc, Czech Republic.|Department of Chemistry and Biochemistry, University of Notre Dame , 251 Nieuwland Science Center, Notre Dame, Indiana 46556, United States.
authors.forename: Viktor
authors.initials: V
authors.lastname: Krchňák
authors.affiliation: Instituto de Química Rosario-IQUIR (CONICET), Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario , Suipacha 531, Rosario S2002LRK, Argentina.
authors.forename: Sebastián A
authors.initials: SA
authors.lastname: Testero
mesh_terms: D000480:Alkynes / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D003500:Cyclization; D006046:Gold / Q000737:chemistry*; D048289:Imidazolidines / Q000138:chemical synthesis*; D015394:Molecular Structure; D054852:Small Molecule Libraries / Q000138:chemical synthesis*; D060327:Solid-Phase Synthesis Techniques
chemical_list: D000480:Alkynes; D048289:Imidazolidines; D054852:Small Molecule Libraries; C004916:ethylene urea; D006046:Gold
keywords: C−N bond formation; gold catalysis; imidazolidin-2-ones; propargylureas; solid-phase synthesis