TY - JOUR
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.
N1 - Publisher Copyright:
© The Royal Society of Chemistry.
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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U2 - 10.1039/c4ob02137a
DO - 10.1039/c4ob02137a
M3 - Article
C2 - 25412895
AN - SCOPUS:84923863394
SN - 1477-0520
VL - 13
SP - 1053
EP - 1067
JO - Organic and Biomolecular Chemistry
JF - Organic and Biomolecular Chemistry
IS - 4
ER -