title: Regioselective synthesis of 3,4,5-trisubstituted 2-aminofurans.
abstract: Three series of methyl 5-substituted 2-aminofuran-4-keto-3-carboxylates have been prepared following a multicomponent reaction strategy by the addition of an isocyanide to 4-oxo-2-butynoate in the presence of an aldehyde. The cycloaddition regioselectivity is generally high (>95%) but decreases when an electron-rich substituent is located at the butynoate 4-position.
authors.affiliation: ICMR, UMR7312-CNRS, Université de Reims Champagne Ardenne, UFR Pharmacie, 51 rue Cognacq Jay, 51096 Reims Cedex, France. clement.denhez@univ-reims.fr.
authors.forename: Thi Ngoc Tram
authors.initials: TN
authors.lastname: Huynh
authors.forename: Pascal
authors.initials: P
authors.lastname: Retailleau
authors.forename: Clément
authors.initials: C
authors.lastname: Denhez
authors.forename: Kim Phi Phung
authors.initials: KP
authors.lastname: Nguyen
authors.forename: Dom
authors.initials: D
authors.lastname: Guillaume
mesh_terms: D000447:Aldehydes / Q000737:chemistry; D002264:Carboxylic Acids / Q000138:chemical synthesis*; D003486:Cyanides / Q000737:chemistry*; D061565:Cycloaddition Reaction; D005229:Fatty Acids, Monounsaturated / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis*; D013237:Stereoisomerism
chemical_list: D000447:Aldehydes; D002264:Carboxylic Acids; D003486:Cyanides; D005229:Fatty Acids, Monounsaturated; D005663:Furans; C057684:fumaraldehydic acid