Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (11): 2993-2999.DOI: 10.6023/cjoc201704037 Previous Articles     Next Articles

Articles

碱促进下空气氧化合成α-羟基苯乙酰胺

张新明, 郭玉军, 陶贵德, 张武   

  1. 安徽师范大学化学与材料科学学院 芜湖 241000
  • 收稿日期:2017-04-22 修回日期:2017-07-03 出版日期:2017-11-25 发布日期:2017-07-07
  • 通讯作者: 张武 E-mail:zhangwu@mail.ahnu.edu.cn
  • 基金资助:

    国家自然科学基金(No.21272006)资助项目.

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

Zhang Xinming, Guo Yujun, Tao Guide, Zhang Wu   

  1. College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000
  • Received:2017-04-22 Revised:2017-07-03 Online:2017-11-25 Published:2017-07-07
  • Contact: 10.6023/cjoc201704037 E-mail:zhangwu@mail.ahnu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21272006).

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 1H NMR, 13C NMR and HRMS. The molecular structure of 2-(2-bromophenyl)-2-hydroxy-N-(p-tolyl)acetamide (2a) was confirmed by using single-crystal X-ray analyses.

Key words: α-hydroxyl amides, aerobic oxidation, synthesis, KOH-DMSO