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Issue 4, 2015
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Synthesis and tautomerization of hydroxylated isoflavones bearing heterocyclic hemi-aminals

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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.

Graphical abstract: Synthesis and tautomerization of hydroxylated isoflavones bearing heterocyclic hemi-aminals

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Publication details

The article was received on 07 Oct 2014, accepted on 13 Nov 2014 and first published on 13 Nov 2014


Article type: Paper
DOI: 10.1039/C4OB02137A
Citation: Org. Biomol. Chem., 2015,13, 1053-1067
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    Synthesis and tautomerization of hydroxylated isoflavones bearing heterocyclic hemi-aminals

    M. S. Frasinyuk, S. P. Bondarenko, V. P. Khilya, C. Liu, D. S. Watt and V. M. Sviripa, Org. Biomol. Chem., 2015, 13, 1053
    DOI: 10.1039/C4OB02137A

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