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

doi:10.6023/cjoc201704037

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

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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

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 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

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

Received:2017-04-22 Revised:2017-07-03 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).

1. Aerobic Oxidation for the Synthesis of N-Substituted α-Hydroxyl Phenylacetamides Promoted by Base.PDF(4164KB)

Abstract

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

Cite this article

Zhang Xinming, Guo Yujun, Tao Guide, Zhang Wu. Aerobic Oxidation for the Synthesis of N-Substituted α-Hydroxyl Phenylacetamides Promoted by Base[J]. Chin. J. Org. Chem., 2017, 37(11): 2993-2999.

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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

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