Oxidative Halocyclization of N-Allylarylamides with KX/Oxone System: Green Synthesis of 5-Halomethyl-2-Oxazolines

doi:10.6023/cjoc202005087

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (12): 4298-4304.DOI: 10.6023/cjoc202005087 Previous Articles Next Articles

KX/Oxone体系实现的N-烯丙基芳酰胺的氧化卤环化反应:5-卤甲基-2-噁唑啉的绿色合成

刘新明^a, 李路^a, 晋李成^a, 赵金灿^b, 华远照^c, 王敏灿^c, 刘澜涛^a,c

a 商丘师范学院化学化工学院河南商丘 476000;
b 河北大学化学与环境科学学院河北保定 071002;
c 郑州大学化学学院郑州 450001

收稿日期:2020-05-29 修回日期:2020-07-02 发布日期:2020-07-23
通讯作者: 刘澜涛, 赵金灿 E-mail:liult05@iccas.ac.cn.;jczhao@hbu.edu.cn
基金资助:
国家自然科学基金（No.21572126）、河南省科技创新人才（No.2018JQ0011）、河北省自然科学基金（No.B2019201415）和中西部高校综合提升工程（No.521000981026）资助项目.

Oxidative Halocyclization of N-Allylarylamides with KX/Oxone System: Green Synthesis of 5-Halomethyl-2-Oxazolines

Liu Xinming^a, Li Lu^a, Jin Licheng^a, Zhao Jincan^b, Hua Yuanzhao^c, Wang Mincan^c, Liu Lantao^a,c

a College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu, Henan 476000;
b College of Chemistry & Environmental Science, Hebei University, Baoding, Hebei 071002;
c College of Chemistry, Zhengzhou University, Zhengzhou 450001

Received:2020-05-29 Revised:2020-07-02 Published:2020-07-23
Supported by:
Project supported by the National Natural Science Foundation of China (No. 21572126), the Program of Science and Technology Innovation Talents of Henan Province (No. 2018JQ0011), the Natural Science Foundation of Hebei Province (No. B2019201415), and the Fundamental Research Funds for the Midwest Universities Comprehensive Strength Promotion Project (No. 521000981026).

1. cjoc202005087.pdf(2525KB)

Abstract

With inexpensive potassium halide (KX) as halogen source, and oxone as oxidant, a series of allylamides underwent halocyclization reaction and generated 5-halomethyl-2-oxazolines in good to excellent isolated yields under mild conditions. The protocol showed attractive advanced features including low cost of halogen source, absence of organic byproduct, and resultant environmental-friendly nature. In addition, various useful derivatives could be expected by proper nucleophilic substitution reactions.

Key words: oxone, halocyclization, oxazolines

Cite this article

Liu Xinming, Li Lu, Jin Licheng, Zhao Jincan, Hua Yuanzhao, Wang Mincan, Liu Lantao. Oxidative Halocyclization of N-Allylarylamides with KX/Oxone System: Green Synthesis of 5-Halomethyl-2-Oxazolines[J]. Chinese Journal of Organic Chemistry, 2020, 40(12): 4298-4304.

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KX/Oxone体系实现的N-烯丙基芳酰胺的氧化卤环化反应:5-卤甲基-2-噁唑啉的绿色合成

Oxidative Halocyclization of N-Allylarylamides with KX/Oxone System: Green Synthesis of 5-Halomethyl-2-Oxazolines

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