Base-Free 5-exo-dig aza-Cyclization of N-Methoxyl-2-alkynylbenzamides in Water

doi:10.6023/cjoc202003016

Chinese Journal of Organic Chemistry ›› 2020, Vol. 40 ›› Issue (7): 2071-2077.DOI: 10.6023/cjoc202003016 Previous Articles Next Articles

水相中无碱条件下N-甲氧基-2-炔基苯甲酰胺的5-外型氮杂环化反应

刘仁志^a,b, 杨民^b, 邱观音生^c, 张莲鹏^d, 王玉超^c, 罗劲^a

a 江西师范大学分析测试中心南昌 330022;
b 赣南医学院基础医学院江西赣州 341000;
c 嘉兴学院生物与化学工程学院南昌 330022;
d 西南林业大学材料科学与工程学院昆明 650224

收稿日期:2020-03-07 修回日期:2020-04-04 发布日期:2020-04-17
通讯作者: 邱观音生, 张莲鹏, 罗劲 E-mail:qiuguanyinsheng@mail.zjxu.edu.cn;lpz@zju.edu.cn;jinluo@jxnu.edu.cn
基金资助:
国家自然科学基金（Nos.21502069，21772067）资助项目.

Base-Free 5-exo-dig aza-Cyclization of N-Methoxyl-2-alkynylbenzamides in Water

Liu Renzhi^a,b, Yang Min^b, Qiu Guanyinsheng^c, Zhang Lianpeng^d, Wang Yuchao^c, Luo Jin^a

a Analytical and Testing Center, Jiangxi Normal University, Nanchang 330022;
b Department of Forensic Science, Gannan Medical University, Ganzhou 341000;
c College of Biological, Chemical Sciences and Engineering, Jiaxing University, Jiaxing 314001;
d School of Materials Science and Engineering, Southwest Forestry University, Kunming 650224 China

Received:2020-03-07 Revised:2020-04-04 Published:2020-04-17
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21772067, 21502069).

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Abstract

A based-free 5-exo-dig aza-cyclization of N-methoxyl-2-alkynylbenzamides in water is reported for the synthesis of various N-methoxylisoindolin-1-ones. The transformation proceeds smoothly with high efficiency and good functional group tolerance. In the process, it is believed that N-methoxyl protecting group serves as "molecular base" to facilitate the formation of amide nitrogen anion. Interestingly, by increasing reaction temperature, a series of N-free-isoindolin-1-ones were also obtained.

Key words: water, N-methoxyl-2-alkynylbenzamide, 5-exo-dig aza-cyclization, isoindolin-1-one

Cite this article

Liu Renzhi, Yang Min, Qiu Guanyinsheng, Zhang Lianpeng, Wang Yuchao, Luo Jin. Base-Free 5-exo-dig aza-Cyclization of N-Methoxyl-2-alkynylbenzamides in Water[J]. Chinese Journal of Organic Chemistry, 2020, 40(7): 2071-2077.

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水相中无碱条件下N-甲氧基-2-炔基苯甲酰胺的5-外型氮杂环化反应

Base-Free 5-exo-dig aza-Cyclization of N-Methoxyl-2-alkynylbenzamides in Water

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