Changchun Institute of Applied Chemistry, Chinese Academy of Sciences, Changchun, 130022, China.
Org Lett. 2012 Jan 20;14(2):644-7. doi: 10.1021/ol203282h. Epub 2012 Jan 3.
A highly regioselective synthesis of 3-arylamino- and 5-arylaminoisoxazoles from enaminones based on reaction condition selection is reported. 3-Arylaminoisoxazoles were produced by treating enaminones with aqueous hydroxylamine in DMF at 100 °C, whereas 5-arylaminoisoxazoles were synthesized by subjecting enaminones to aqueous hydroxylamine in the presence of KOH and TBAB in water under reflux. A mechanism for the regioselective synthesis of 3-arylamino- and 5-arylaminoisoxazoles is proposed.
本文报道了一种基于反应条件选择的，从烯胺酮出发高区域选择性合成 3-芳氨基-和 5-芳氨基异恶唑的方法。在 100°C 下，用 DMF 中的水合羟胺处理烯胺酮可以得到 3-芳氨基异恶唑，而用 KOH 和 TBAB 在水中回流处理烯胺酮可以得到 5-芳氨基异恶唑。提出了一种 3-芳氨基-和 5-芳氨基异恶唑区域选择性合成的反应机理。
