Synthesis and tautomerization of hydroxylated isoflavones bearing heterocyclic hemi-aminals

Mykhaylo S. Frasinyuk, Svitlana P. Bondarenko, Volodymyr P. Khilya, Chunming Liu, David S. Watt, Vitaliy M. Sviripa

Research output: Contribution to journalArticlepeer-review

16 Scopus citations

Abstract

The aminomethylation of hydroxylated isoflavones with 2-aminoethanol, 3-amino-1-propanol, 4-amino-1-butanol, and 5-amino-1-pentanol in the presence of excess formaldehyde led principally to 9-(2-hydroalkyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]-oxazin-4-ones 4 and/or the tautomeric 7-hydroxy-8-(1,3-oxazepan-3-ylmethyl)-4H-chromen-4-ones 5. The ratio of these tautomers was dependent on solvent polarity, electronic effects of aryl substituents in the isoflavone and the structure of the amino alcohol. NMR studies confirmed the interconversion of tautomeric forms.

Original languageEnglish
Pages (from-to)1053-1067
Number of pages15
JournalOrganic and Biomolecular Chemistry
Volume13
Issue number4
DOIs
StatePublished - Jan 28 2015

Bibliographical note

Publisher Copyright:
© The Royal Society of Chemistry.

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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