Citation: Liu Renzhia, 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. doi: 10.6023/cjoc202003016 shu

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

Liu Renzhia ^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, hemical Sciences and Engineering, Jiaxing University, Jiaxing 314001
d.
School of Materials Science and Engineering, Southwest Forestry University, Kunming 650224 China

Corresponding author: Qiu Guanyinsheng, qiuguanyinsheng@mail.zjxu.edu.cn Zhang Lianpeng, lpz@zju.edu.cn Luo Jin, jinluo@jxnu.edu.cn
Received Date: 7 March 2020
Revised Date: 4 April 2020
Available Online: 17 April 2020
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 21772067, 21502069)the National Natural Science Foundation of China (Nos. 21772067, 21502069)

Figures(4)

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.
- water,
- N-methoxyl-2-alkynylbenzamide,
- 5-exo-dig aza-cyclization,
- isoindolin-1-one
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