Hao Wen-Juan, Jiang Bo, Tu Shu-Jiang, Wu Shan-Shan, Han Zheng-Guo, Cao Xu-Dong, Zhang Xiao-Hong, Yan Shu, Shi Feng
School of Chemistry and Chemical Engineering, Xuzhou Normal University, Key Laboratory of Biotechnology for Medicinal Plant, Xuzhou, Jiangsu 221116, PR China.
J Comb Chem. 2009 Mar 9;11(2):310-4. doi: 10.1021/cc800175n.
A series of new 3-pyrimidin-5-ylpropanamides was selectively synthesized via a microwave-assisted, chemoselective reaction of arylidene-Meldrum's acid, 6-hydroxypyrimidin-4(3H)-one, and structurally diverse amines including (S or R)-1-phenylethanamine, cyclohexanamine, and cyclopentanamine depended on nature of solvents. In this reaction, the utilization of HOAc as a solvent leads to 3-pyrimidin-5-ylpropanamides, whereas water as reaction media results in the spiro[5.5]undecane-1,5,9-triones from same starting materials. This method has the advantages of short synthetic route, operational simplicity, increased safety for small-scale high-speed synthesis, and minimal environment impact.
通过微波辅助的、芳叉基丙二酸亚异丙酯、6-羟基嘧啶-4(3H)-酮与包括(S或R)-1-苯乙胺、环己胺和环戊胺在内的结构多样的胺的化学选择性反应，根据溶剂的性质选择性地合成了一系列新的3-嘧啶-5-基丙酰胺。在该反应中，使用乙酸作为溶剂会生成3-嘧啶-5-基丙酰胺，而以水作为反应介质时，相同的起始原料会生成螺[5.5]十一烷-1,5,9-三酮。该方法具有合成路线短、操作简便、小规模高速合成安全性提高以及对环境影响最小等优点。
