Study of Oxidation of N-Sulfonylimines into Oxaziridines Catalyzed by Ammonium Halides

doi:10.6023/cjoc201606005

Chin. J. Org. Chem. ›› 2017, Vol. 37 ›› Issue (1): 116-121.DOI: 10.6023/cjoc201606005 Previous Articles Next Articles

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卤化铵催化氧化磺酰亚胺为哑嗪的方法研究

姚秋丽, 黄晓丽, 蒲家志, 席先秀, 方学红, 赵玲, 麦有群, 贺春阳

遵义医学院药学院遵义 563000

收稿日期:2016-06-02 修回日期:2016-09-08 发布日期:2016-09-12
通讯作者: 姚秋丽 E-mail:yaoqiuli@zmc.edu.cn
基金资助:
国家自然科学基金（No. 21462056）、贵州省联合基金（No.[2014]7542）、贵州省科技创新团队（No.[2014]4002）、贵州省大学生创新计划（No. 201413653013）、遵义医学院（No. F-627）资助项目.

Study of Oxidation of N-Sulfonylimines into Oxaziridines Catalyzed by Ammonium Halides

Yao Qiuli, Huang Xiaoli, Pu Jiazhi, Xi Xianxiu, Fang Xuehong, Zhao Ling, Mai Youqun, He Chunyang

School of Pharmacy, Zunyi Medical University, Zunyi 563000

Received:2016-06-02 Revised:2016-09-08 Published:2016-09-12
Supported by:
Project supported by the National Natural Science Foundation of China(No. 21462056), the Science and Technology Foundation of Guizhou Province(Nos.[2014]7542,[2014]4002), the Education Department of Guizhou Province(No. 201413653013), and the Zunyi Medical University(No. F-627).

The method of oxidation of N-sulfonylimines to N-sulfonyloxaziridines with m-chloroperbenzoic acid catalyzed by ammonium halides was systematically investigated for the first time.Tetraethylammonium halides(Et₄NI or Et₄NCl) and tet-ramethylammonium halides(Me₄NI,Me₄NBr or Me₄NCl) were firstly used to catalyze the oxidation of a series of N-sulfonylimines to the corresponding N-sulfonyloxaziridines in excellent yields.The experimental results showed that the alkyl group of the ammonium had significant influence on the reaction,whereas the halide ions had lesser influence on the reaction.Thus the research has provided a simple procedure for the preparation of oxaziradine with excellent yields.

Key words: ammonium halides, N-sulfonyloxaziridines, oxaziridines, m-chloroperbenzoic acid

Cite this article

Yao Qiuli, Huang Xiaoli, Pu Jiazhi, Xi Xianxiu, Fang Xuehong, Zhao Ling, Mai Youqun, He Chunyang. Study of Oxidation of N-Sulfonylimines into Oxaziridines Catalyzed by Ammonium Halides[J]. Chin. J. Org. Chem., 2017, 37(1): 116-121.

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卤化铵催化氧化磺酰亚胺为哑嗪的方法研究

Study of Oxidation of N-Sulfonylimines into Oxaziridines Catalyzed by Ammonium Halides

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