A new synthesis of 5-arylbenzo[c]xanthones from photoinduced electrocyclisation and oxidation of (E)-3-styrylflavones

Djenisa H.A. Rocha, Diana C.G.A. Pinto, Artur M.S. Silva, Tamás Patonay, José A.S. Cavaleiro

Research output: Contribution to journalArticle

12 Citations (Scopus)

Abstract

A new synthetic route to 5-arylbenzo[c]xanthones is -established. This was accomplished by use the Heck reaction of 3-bromoflavones with styrene derivatives, leading to (E)-3-styrylflavones with total diastereoselectivity. This transformation was greatly improved under microwave irradiation. The one-pot, photoinduced electrocyclisation of (E)-3-styrylflavones and further in situ oxidation of the cycloadduct leads to 5-arylbenzo[c]xan-thones.

Original languageEnglish
Pages (from-to)559-564
Number of pages6
JournalSynlett
Issue number4
DOIs
Publication statusPublished - Feb 14 2012

Keywords

  • Heck reaction
  • microwave irradiation
  • oxidation
  • photocyclisation

ASJC Scopus subject areas

  • Organic Chemistry

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