碱促进下空气氧化合成α-羟基苯乙酰胺

Aerobic Oxidation for the Synthesis of N-Substituted α-Hydroxyl Phenylacetamides Promoted by Base

α-羟基酰胺类化合物具有独特的药理和生理活性,引起了有机化学家和药物化学家的广泛关注.目前,这类化合物的合成主要是通过α-羟基苯乙酸的胺基化反应,或者是通过还原α-羰基酰胺类化合物而得到.本工作通过在KOH-DMSO(二甲基亚砜)体系中,利用空气为氧化剂,发展了一种简单高效地制备α-羟基酰胺类化合物的方法.共得到21个α-羟基酰胺产物,并对这些化合物进行了结构表征,其中N-对甲苯基-2-(2-溴苯基)-2-羟基乙酰胺(2a)的结构还通过X射线单晶衍射分析确认.

α-Hydroxyl amides are important skeleton and valuable intermediates that present in many natural products,pharmaceutical active compounds,and organic functional materials.The main methods for synthesis of α-hydroxyl amides are either through amidation of α-hydroxyl acids,or by reduction of α-keto amides.Herein,a convenient potassium hydroxide/dimethyl sulfoxide promoted aerobic oxidation reaction to prepare N-substituted α-hydroxyl phenylacetamides is reported in good to high yields.21 corresponding products were obtained and characterized by 1 H NMR,13 C NMR and HRMS.The molecular structure of 2-（2-bromophenyl）-2-hydroxy-N-（p-tolyl）acetamide（2 a） was confirmed by using single-crystal X-ray analyses.