含杂环半缩醛胺的羟基化异黄酮的合成与互变异构
Synthesis and tautomerization of hydroxylated isoflavones bearing heterocyclic hemi-aminals.
作者信息
Frasinyuk Mykhaylo S, Bondarenko Svitlana P, Khilya Volodymyr P, Liu Chunming, Watt David S, Sviripa Vitaliy M
机构信息
Department of Molecular and Cellular Biochemistry, College of Medicine, University of Kentucky, Lexington, KY 40536-0509, USA.
出版信息
Org Biomol Chem. 2015 Jan 28;13(4):1053-67. doi: 10.1039/c4ob02137a. Epub 2014 Nov 21.
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.
摘要
在过量甲醛存在下，用2-氨基乙醇、3-氨基-1-丙醇、4-氨基-1-丁醇和5-氨基-1-戊醇对羟基化异黄酮进行氨甲基化反应，主要生成9-(2-羟烷基)-9,10-二氢-4H,8H-色烯并[8,7-e][1,3]-恶嗪-4-酮4和/或互变异构的7-羟基-8-(1,3-恶庚环-3-基甲基)-4H-色烯-4-酮5。这些互变异构体的比例取决于溶剂极性、异黄酮中芳基取代基的电子效应以及氨基醇的结构。核磁共振研究证实了互变异构形式的相互转化。
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