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

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.

SUBMITTER: Frasinyuk MS

PROVIDER: S-EPMC5571763 | biostudies-literature | 2015 Jan

REPOSITORIES: biostudies-literature

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

Frasinyuk Mykhaylo S MS Bondarenko Svitlana P SP Khilya Volodymyr P VP Liu Chunming C Watt David S DS Sviripa Vitaliy M VM

Organic & biomolecular chemistry 20141121 4

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 alc ...[more]

PMID: 25412895

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