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

Research output: Contribution to journalArticle

32 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)1619-1628
Number of pages10
JournalHeterocycles
Volume63
Publication statusPublished - 2004

    Fingerprint

All Science Journal Classification (ASJC) codes

  • Analytical Chemistry
  • Pharmacology
  • Organic Chemistry

Cite this