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在氟化钾作催化剂和四氢呋喃作溶剂的条件下,研究了系列脂肪胺亲核试剂与5-烷氧基-3,4-二卤-2(5H)-呋喃酮发生的反应,通过旋光度,UV-Vis,IR,1H NMR,13C NMR,MS,元素分析和X射线单晶衍射等表征方法对产物进行结构表征,发现通常情况下发生预期的串联迈克尔加成-消除反应,合成了13个新的β-胺基-2(5H)-呋喃酮.但是,空间位阻较大的二环己基胺与5-烷氧基-3,4-二卤-2(5H)-呋喃酮反应时,却得到了4个异常的2(5H)-呋喃酮开环产物,其可能是经开环重排反应的机理得到的.
In the presence of potassium fluoride as catalyst and tetrahydrofuran as solvent, the reaction of a series of aliphatic amine nucleophiles with 5-alkoxy-3,4-dihalo-2 (5H) -furanones was studied. The structures were characterized by UV-Vis, IR, 1H NMR, 13C NMR, MS, elemental analysis and single crystal X-ray diffraction. It was found that in general the expected tandem Michael addition-elimination reaction occurred and 13 Of novel β-amino-2 (5H) -furanones. However, sterically hindered dicyclohexylamine reacted with 5-alkoxy-3,4-dihalo-2 (5H) , Four unusual 2 (5H) -furanone ring-opening products were obtained, which may be obtained by the mechanism of ring-opening rearrangement reaction.