Oxidation of enol acetate of flavanone with thallium(III) nitrate or phenyliodonium diacetate: A convenient new route to isoflavone and flavone

István Németh, Attila Kiss-Szikszai, Katalin Gulácsi, Attila Mándi, I. Komáromi, T. Kurtán, S. Antus

Research output: Contribution to journalArticle

Abstract

A new high-yield method has been described for the preparation of isoflavone by oxidation of enol acetate of flavanone with thallium(III) nitrate or phenyliodonium diacetate in trimethyl orthoformate in the presence of 70 % perchloric acid at room temperature. Flavone could also be prepared in high yield from the enol acetate by oxidation with the same reagents in glacial acetic acid at room temperature. Some key intermediates of these oxidations were investigated with quantum chemical (HF and DFT) methods. Graphical Abstract: [Figure not available: see fulltext.].

Original languageEnglish
Pages (from-to)849-855
Number of pages7
JournalMonatshefte fur Chemie
Volume145
Issue number5
DOIs
Publication statusPublished - 2014

Fingerprint

flavone
Isoflavones
Thallium
Nitrates
Acetates
Oxidation
Discrete Fourier transforms
Acetic Acid
Temperature
flavanone
phenyliodonium

Keywords

  • Dehydrogenation
  • Neighboring group participation
  • Phenyl migration
  • Solvent effect

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Oxidation of enol acetate of flavanone with thallium(III) nitrate or phenyliodonium diacetate : A convenient new route to isoflavone and flavone. / Németh, István; Kiss-Szikszai, Attila; Gulácsi, Katalin; Mándi, Attila; Komáromi, I.; Kurtán, T.; Antus, S.

In: Monatshefte fur Chemie, Vol. 145, No. 5, 2014, p. 849-855.

Research output: Contribution to journalArticle

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