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 perfluoroaryl- substituent 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.

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(7), 1619-1628 [10.3987/COM-04-10059].

Fluorinated heterocyclic compounds. A photochemical approach to a synthesis of fluorinated quinazolin-4-ones

BUSCEMI, Silvestre;PACE, Andrea;PALUMBO PICCIONELLO, Antonio;PIBIRI, Ivana;VIVONA, Nicolo'
2004

Abstract

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 perfluoroaryl- substituent 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.
Settore CHIM/06 - Chimica Organica
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(7), 1619-1628 [10.3987/COM-04-10059].
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Utilizza questo identificativo per citare o creare un link a questo documento: https://hdl.handle.net/10447/20318
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