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

doi:10.1039/c4ob02137a

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

Molecular and Cellular Biochemistry

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15 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 language	English
Pages (from-to)	1053-1067
Number of pages	15
Journal	Organic and Biomolecular Chemistry
Volume	13
Issue number	4
DOIs	https://doi.org/10.1039/c4ob02137a
State	Published - Jan 28 2015

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© The Royal Society of Chemistry.

ASJC Scopus subject areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1039/c4ob02137a

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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.",

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T1 - Synthesis and tautomerization of hydroxylated isoflavones bearing heterocyclic hemi-aminals

AU - Frasinyuk, Mykhaylo S.

AU - Bondarenko, Svitlana P.

AU - Khilya, Volodymyr P.

AU - Liu, Chunming

AU - Watt, David S.

AU - Sviripa, Vitaliy M.

PY - 2015/1/28

Y1 - 2015/1/28

N2 - 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.

AB - 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.

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Synthesis and tautomerization of hydroxylated isoflavones bearing heterocyclic hemi-aminals

Abstract

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