Fluorinated Heterocyclic Compounds. A Photochemical Approach to a Synthesis of Fluorinated Quinazolin-4-ones
- 1 January 2004
- journal article
- Published by The Japan Institute of Heterocyclic Chemistry in HETEROCYCLES
- Vol. 63 (7) , 1619
- https://doi.org/10.3987/com-04-10059
Abstract
An efficient and generalized photochemical methodology for the\ud preparation of fluorinated quinazolin-4-ones is described. Depending on the\ud starting substrate, quinazolin-4-ones bearing a perfluoroalkyl- or perfluoroarylsubstituent\ud in position 2 or fluorine atoms on any positions of the benzo-fused\ud moiety can easily be obtained. 5-Aryl-3-perfluoroalkylpentafluorophenyl- or 5-\ud polyfluoroaryl-3-phenyl(methyl)-1,2,4-oxadiazoles, respectively, can be\ud considered as ideal precursors that can be transformed into the target quinazolin-\ud 4-ones by irradiation in the presence of triethylamine (TEA) (at λ = 313 nm) or\ud pyrene (at λ = 365 nm) in dry methanol or acetonitrile as solvent. Some\ud mechanistic considerations confirm the involvement of a photoinduced electron\ud transfer processKeywords
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