Selenium Radical-Triggered Spiro-Tricyclization of N-Aryl-N-(2-hydroxyethyl)propiolamides

Feng Pan; Huilin Xie; Wenlin Xie; Yu-Chao Wang; Jin-Biao Liu; Guanyinsheng Qiu

doi:10.1055/a-1775-2910

Synthesis, Inhaltsverzeichnis

Synthesis 2022; 54(13): 3105-3113
DOI: 10.1055/a-1775-2910

paper

Selenium Radical-Triggered Spiro-Tricyclization of N-Aryl-N-(2-hydroxyethyl)propiolamides

Feng Pan‡

^aSchool of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, P. R. of China

^bCollege of Biological, Chemical Science and Engineering, Jiaxing University, Jiaxing 314001, Zhejiang, P. R. of China

,

Huilin Xie‡

^cFaculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 34100, P. R. of China

,

Wenlin Xie∗

^aSchool of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan 411201, P. R. of China

,

Yu-Chao Wang

^bCollege of Biological, Chemical Science and Engineering, Jiaxing University, Jiaxing 314001, Zhejiang, P. R. of China

^cFaculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 34100, P. R. of China

,

Jin-Biao Liu ∗

^cFaculty of Materials Metallurgy and Chemistry, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou 34100, P. R. of China

,

Guanyinsheng Qiu ∗

^bCollege of Biological, Chemical Science and Engineering, Jiaxing University, Jiaxing 314001, Zhejiang, P. R. of China

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Abstract

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Abstract

A blue LED-promoted dearomative oxo-spirocyclization of N-aryl-N-(2-hydroxyethyl)propiolamides is developed. The reaction works well to provide a series of selenium-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones with high efficiency and good tolerance for functional groups. Besides, diselenium-containing benzo[b]pyrrolo[2,1-c][1,4]oxazine-3,9-diones can also be efficiently synthesized in the presence of Oxone. In this process, it is believed that a selenium radical-triggered ipso-cyclization and oxo-Michael addition are involved. Further applications using the prepared products in bioactivity assay is currently underway.

Key words

selenium radical - dearomative oxo-spirocyclization - propiolamides - ipso-cyclization - α-addition

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Referenzen

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