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Chinese Journal of Organic Chemistry >

2020 , Vol. 40 >Issue 7: 2071 - 2077

DOI: https://doi.org/10.6023/cjoc202003016

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

  • Liu Renzhi ,
  • Yang Min ,
  • Qiu Guanyinsheng ,
  • Zhang Lianpeng ,
  • Wang Yuchao ,
  • Luo Jin
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  • 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 date: 2020-03-07

  Revised date: 2020-04-04

  Online 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 . DOI: 10.6023/cjoc202003016

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