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Current Chinese Science

Author(s): Xiya Cheng, Xiaoyang Yan, Meng Li, Sarita Yadav, Yanfei Lin* and Guanyinsheng Qiu*

DOI: 10.2174/2210298102666220524151115

Cite As
Manganese-Catalyzed Radical 6-endo Azacyclization of 2-Alkynylbenzamide for the Synthesis of 3-Hydroxylisoquinolin-1,4-dione

Page: [400 - 406] Pages: 7

  • * (Excluding Mailing and Handling)

Abstract

Background: The versatile 2-alkynylbenzamde has been reported to produce many privileged skeletons, like isoquinolin-1-ones, isocoumarin-1-imines, isoindolin-1-ones, and isobenzofuran- 1-imines. Recently, we reported the projected transformation using copper salt (CuCl2) as a catalyst under the O2 atmosphere. To expand the scope of the reaction, we used another inexpensive metal salt, MnO2, as a catalyst.

Methods: The paper aims to explore a manganese-catalyzed reaction of 2-alkynylbenzamide under an O2 balloon for the synthesis of 3-hydroxylisoquinolin-1,4-dione.

Results: Results on reaction scope shows the 10 mol% MnO2 in O2 atmosphere and DCE solvent catalyzed the cyclization of 2-alkynylbenzamide to produce 3-hydroxylisoquinolin-1,4-diones in 40-68% isolated yields. The reaction proceeds through a regioselective N-center radical 6-endo-dig aza-cyclization pathway.

Conclusion: We have developed a manganese-catalyzed cyclization of 2-alkynlbenzamide for the synthesis of 3-hydroxylisoquinolin-1,4-diones under an O2 balloon. It is believed that the N-center radical-based 6-endo dig aza-cyclization proceeded in a regioselective manner.

Keywords: 2-Alkynylbenzamide, manganese catalysis, hydroxyliosoquinolin-1, 4-dione, 6-endo-dig cyclization, catalyst, MnO2.

Graphical Abstract

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