title: Aminocarbonylation of 4-iodo-1H-imidazoles with an amino acid amide nucleophile: synthesis of constrained H-Phe-Phe-NH2 analogues.
abstract: A simple and an expedient process to prepare 5-aryl-1-benzyl-1H-imidazole-4-carboxamides by the aminocarbonylation of 5-aryl-4-iodo-1H-imidazoles using ex situ generation of CO from Mo(CO)6 with an amino acid amide nucleophile is reported. Furthermore, a microwave-assisted protocol for the direct C-5 arylation of 1-benzyl-1H-imidazole and a regioselective C-4 iodination method to acquire starting material for our aminocarbonylation are presented. The method can be used to prepare imidazole based peptidomimetics, herein exemplified by the synthesis of constrained H-Phe-Phe-NH2 analogues.
authors.affiliation: Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, Uppsala Biomedical Center, Uppsala University , P.O. Box 574, SE-751 23 Uppsala, Sweden.
authors.forename: Anna
authors.initials: A
authors.lastname: Skogh
authors.forename: Rebecca
authors.initials: R
authors.lastname: Fransson
authors.forename: Christian
authors.initials: C
authors.lastname: Sköld
authors.forename: Mats
authors.initials: M
authors.lastname: Larhed
authors.forename: Anja
authors.initials: A
authors.lastname: Sandström
mesh_terms: D000577:Amides / Q000737:chemistry*; D000596:Amino Acids / Q000737:chemistry*; D007093:Imidazoles / Q000737:chemistry*; D015394:Molecular Structure; D010446:Peptide Fragments / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000577:Amides; D000596:Amino Acids; D007093:Imidazoles; D010446:Peptide Fragments