New insight into the ring contraction of 2′-benzyloxyflavanones

István Németh, Katalin Gulácsi, Sándor Antus, Sándor Kéki, Miklós Zsuga

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The reactions of 2′-benzyloxyflavanones 9b,c with thallium(III) nitrate or iodobenzene diacetate in the presence of perchloric or sulfuric acid in trimethyl orthoformate was studied. Depending on the substitution pattern and the conditions, these compounds underwent 2-Aryl migration (9b → 11a) and/or ring contraction (9c → 10b + 11b) and dehydrogenation (9c → 12). A probable mechanism of these transformations is discussed.

Original languageEnglish
Pages (from-to)991-996
Number of pages6
JournalNatural product communications
Volume1
Issue number11
Publication statusPublished - Jan 1 2006

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Keywords

  • 2 3-dihydrobenzo[b]furans
  • 2′-benzyloxyflavanones
  • 2′-benzyloxyisoflavones
  • Aryl migration
  • Ring-contraction

ASJC Scopus subject areas

  • Pharmacology
  • Plant Science
  • Drug Discovery
  • Complementary and alternative medicine

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