Citation: Zhang Xinming, Guo Yujun, Tao Guide, Zhang Wu. Aerobic Oxidation for the Synthesis of N-Substituted α-Hydroxyl Phenylacetamides Promoted by Base[J]. Chinese Journal of Organic Chemistry, ;2017, 37(11): 2993-2999. doi: 10.6023/cjoc201704037 shu

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

College of Chemistry and Materials Science, Anhui Normal University, Wuhu 241000

Corresponding author: Zhang Wu, zhangwu@mail.ahnu.edu.cn
Received Date: 22 April 2017
Revised Date: 3 July 2017
Available Online: 7 November 2017
Fund Project: the National Natural Science Foundation of China 21272006Project supported by the National Natural Science Foundation of China (No. 21272006)

Figures(3)

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.
- α-hydroxyl amides,
- aerobic oxidation,
- synthesis,
- KOH-DMSO
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