title: Formation of γ-oxoacids and 1H-pyrrol-2(5H)-ones from α,β-unsaturated ketones and ethyl nitroacetate.
abstract: Michael addition of ethyl nitroacetate on α,β-unsaturated ketones followed by Nef oxidation under hydrolytic conditions yields γ-oxoacids instead of the corresponding α,δ-dioxoesters. A concerted decarboxylation step is proposed on the basis of computational results. Finally, conversion of the γ-ketoacids thus prepared into 1H-pyrrol-2(5H)-ones by reaction with primary amines under Paal-Knorr conditions is also reported.
authors.affiliation: Kimika Fakultatea, Kimika Organikoa I Saila, Universidad del País Vasco-Euskal Herriko Uniberstitatea, Manuel de Lardizabal Etorbidea 3, 20018 San Sebastián-Donostia, Spain.
authors.forename: Maialen
authors.initials: M
authors.lastname: Aginagalde
authors.forename: Tamara
authors.initials: T
authors.lastname: Bello
authors.forename: Carme
authors.initials: C
authors.lastname: Masdeu
authors.forename: Yosu
authors.initials: Y
authors.lastname: Vara
authors.forename: Ana
authors.initials: A
authors.lastname: Arrieta
authors.forename: Fernando P
authors.initials: FP
authors.lastname: Cossío
mesh_terms: D000085:Acetates / Q000737:chemistry*; D000143:Acids / Q000737:chemistry; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D009574:Nitro Compounds / Q000737:chemistry*; D010100:Oxygen / Q000737:chemistry*; D011758:Pyrroles / Q000737:chemistry*
chemical_list: D000085:Acetates; D000143:Acids; D007659:Ketones; D009574:Nitro Compounds; D011758:Pyrroles; C555739:ethyl nitroacetate; D010100:Oxygen