New insight into the ring contraction of 2′-benzyloxyflavanones

István Németh, Katalin Gulácsi, S. Antus, S. Kéki, M. 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 - 2006

Fingerprint

thallium
perchloric acid
sulfuric acid
nitrates
dehydrogenation
iodobenzene
thallium nitrate

Keywords

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

ASJC Scopus subject areas

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

Cite this

New insight into the ring contraction of 2′-benzyloxyflavanones. / Németh, István; Gulácsi, Katalin; Antus, S.; Kéki, S.; Zsuga, M.

In: Natural Product Communications, Vol. 1, No. 11, 2006, p. 991-996.

Research output: Contribution to journalArticle

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