A versatile synthesis of fluorinated uracils in solution and on solid-phase.
[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.
Fustero
Santos
S
Departamento de Química Orgánica, Universidad de Valencia, E-46100 Burjassot, Spain. santos.fustero@uv.es
Piera
Julio
J
Sanz-Cervera
Juan F
JF
Catalán
Silvia
S
Ramírez de Arellano
Carmen
C
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*
D006845:Hydrocarbons, Fluorinated; D017953:Isocyanates; D017879:Isothiocyanates; D009570:Nitriles; D012996:Solutions; D014498:Uracil