论文部分内容阅读
以对甲基苯乙酮、芳香醛和乙腈为主要原料,通过三氟乙酸催化的改进的Dakin-West反应,顺利得到28个N-[3-(4-甲基苯基)-3-氧代-1-芳基丙基]乙酰胺,最高收率可达95%.18个新化合物的结构经1H NMR,13C NMR和HRMS证实.结构测试发现,羟基苯甲醛参与Dakin-West反应后得到的全部是羟基乙酰化的产物.作者首次证实,羟基苯甲醛参与的Dakin-West反应不是串联反应,而是羟基苯甲醛首先经TFA催化转化为乙酰氧基苯甲醛,然后参与Dakin-West反应,最终生成羟基乙酰化产物.通过碱性水解,可以选择性高收率地制备对应的羟基化β-乙酰氨基酮,同时也反证了羟基乙酰化产物的存在.该研究扩展了TFA催化的Dakin-West反应,为β-乙酰氨基酮的合成提供了新的方法.
Using p-methylacetophenone, aromatic aldehyde and acetonitrile as main raw materials, 28 N- [3- (4-methylphenyl) -3-oxo- 1-arylpropyl] acetamide with the highest yield of 95%. The structures of the 18 new compounds were confirmed by 1H NMR, 13C NMR and HRMS. Structural tests showed that hydroxybenzaldehyde was involved in Dakin-West reaction Is the product of hydroxyacetylation.The authors first confirmed that the Dakin-West reaction involving hydroxybenzaldehyde was not a tandem reaction but that hydroxybenzaldehyde was first converted to acetoxybenzaldehyde by TFA and then involved in the Dakin-West reaction, The final hydroxy acetylated products generated by alkaline hydrolysis can be selectively prepared with high yield of hydroxylated β-acetylamino ketone, but also testifies the existence of hydroxyacetylated products.This study extends the TFA-catalyzed Dakin- West reaction, which provides a new method for the synthesis of β-acetamidone.