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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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Article information


Submitted
07 Oct 2014
Accepted
13 Nov 2014
First published
13 Nov 2014

Org. Biomol. Chem., 2015,13, 1053-1067
Article type
Paper

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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