An efficient and generalized photochemical methodology for the preparation of fluorinated quinazolin-4-ones is described. Depending on the starting substrate, quinazolin-4-ones bearing a perfluoroalkyl- or perfluoroarylsubstituent in position 2 or fluorine atoms on any positions of the benzo-fused moiety can easily be obtained. 5-Aryl-3-perfluoroalkylpentafluorophenyl- or 5- polyfluoroaryl-3-phenyl(methyl)-1,2,4-oxadiazoles, respectively, can be considered as ideal precursors that can be transformed into the target quinazolin- 4-ones by irradiation in the presence of triethylamine (TEA) (at λ = 313 nm) or pyrene (at λ = 365 nm) in dry methanol or acetonitrile as solvent. Some mechanistic considerations confirm the involvement of a photoinduced electron transfer process.
|Data di pubblicazione:||2004|
|Titolo:||Fluorinated heterocyclic compounds. A photochemical approach to a synthesis of fluorinated quinazolin-4-ones|
|Autori:||BUSCEMI S; PACE A; PALUMBO PICCIONELLO A; PIBIRI I; VIVONA N|
|Tipologia:||Articolo su rivista|
|Citazione:||BUSCEMI S, PACE A, PALUMBO PICCIONELLO A, PIBIRI I, & VIVONA N (2004). Fluorinated heterocyclic compounds. A photochemical approach to a synthesis of fluorinated quinazolin-4-ones. HETEROCYCLES, 63, 1619-1628.|
|Digital Object Identifier (DOI):||10.3987/COM-04-10059|
|Appare nelle tipologie:||01 - Articolo su rivista|