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Synthesis 2022; 54(13): 3105-3113
DOI: 10.1055/a-1775-2910
DOI: 10.1055/a-1775-2910
paper
Selenium Radical-Triggered Spiro-Tricyclization of N-Aryl-N-(2-hydroxyethyl)propiolamides
Financial supports from the Natural Science Foundation of Zhejiang Province (Nos. LY22B020010) and the Natural Science Foundation of China (Nos. 21772067, 21801096, and 22161043) are gratefully acknowledged.
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-additionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-1775-2910.
- Supporting Information
Publication History
Received: 26 January 2022
Accepted after revision: 17 February 2022
Accepted Manuscript online:
17 February 2022
Article published online:
02 May 2022
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