title: Multicomponent Synthesis of Uracil Analogues Promoted by Pd-Catalyzed Carbonylation of α-Chloroketones in the Presence of Isocyanates and Amines.
abstract: A short and efficient one-pot synthesis of uracil derivatives with a high structural variability is described. The process is a multicomponent reaction based on a palladium-catalyzed carbonylation of α-chloroketones in the presence of primary amines and isocyanates. In most cases, when the formation of unsymmetrical N,N'-disubstituted uracil derivatives can occur, the methodology demonstrates to be highly regioselective. A mechanistic hypothesis involving β-dicarbonyl palladium intermediates and urea derivatives, generated in situ, has been discussed.
authors.affiliation: †Dipartimento di Scienze e Tecnologie Biologiche ed Ambientali, Università del Salento, Prov.le Lecce-Monteroni, Lecce 73100, Italy.
authors.forename: Serena
authors.initials: S
authors.lastname: Perrone
authors.affiliation: †Dipartimento di Scienze e Tecnologie Biologiche ed Ambientali, Università del Salento, Prov.le Lecce-Monteroni, Lecce 73100, Italy.
authors.forename: Martina
authors.initials: M
authors.lastname: Capua
authors.affiliation: ‡Dipartimento di Farmacia-Scienze del Farmaco, Università degli Studi di Bari "Aldo Moro", Consorzio C.I.N.M.P.I.S., Via E. Orabona 4, Bari 70125, Italy.
authors.forename: Antonio
authors.initials: A
authors.lastname: Salomone
authors.affiliation: †Dipartimento di Scienze e Tecnologie Biologiche ed Ambientali, Università del Salento, Prov.le Lecce-Monteroni, Lecce 73100, Italy.
authors.forename: Luigino
authors.initials: L
authors.lastname: Troisi
mesh_terms: D000588:Amines / Q000737:chemistry*; D002384:Catalysis; D017953:Isocyanates / Q000737:chemistry*; D007982:Levulinic Acids / Q000737:chemistry*; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D014498:Uracil / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D000588:Amines; D017953:Isocyanates; D007982:Levulinic Acids; D014498:Uracil; D010165:Palladium; C021959:2-amino-4-oxo-5-chloropentanoate