title: A versatile synthesis of fluorinated uracils in solution and on solid-phase.
abstract: [reaction: see text] An efficient and convenient two-step synthesis of new fluorinated uracils is described. The first step involves the condensation of an ester enolate with a fluorinated nitrile to furnish fluorinated beta-enamino esters. In turn, these compounds react with organic isocyanates or isothiocyanates to give C-6 fluorinated uracils or thiouracils, respectively, in excellent yields. This synthesis has been successfully adapted to solid-phase conditions with high diversity, thereby facilitating the creation of small (thio)uracil libraries.
authors.affiliation: Departamento de Química Orgánica, Universidad de Valencia, E-46100 Burjassot, Spain. santos.fustero@uv.es
authors.forename: Santos
authors.initials: S
authors.lastname: Fustero
authors.forename: Julio
authors.initials: J
authors.lastname: Piera
authors.forename: Juan F
authors.initials: JF
authors.lastname: Sanz-Cervera
authors.forename: Silvia
authors.initials: S
authors.lastname: Catalán
authors.forename: Carmen
authors.initials: C
authors.lastname: Ramírez de Arellano
mesh_terms: D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis* / Q000737:chemistry; D017953:Isocyanates / Q000737:chemistry; D017879:Isothiocyanates / Q000737:chemistry; D015394:Molecular Structure; D009570:Nitriles / Q000737:chemistry; D012996:Solutions / Q000737:chemistry*; D014498:Uracil / Q000031:analogs & derivatives* / Q000138:chemical synthesis*
chemical_list: D006845:Hydrocarbons, Fluorinated; D017953:Isocyanates; D017879:Isothiocyanates; D009570:Nitriles; D012996:Solutions; D014498:Uracil