Accessing 3,4-Dihydroquinolinone from N-Arylacrylamides via Tetralone-Mediated Energy Transfer and 1,3-Hydrogen Shift,Organic Letters

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Accessing 3,4-Dihydroquinolinone from N-Arylacrylamides via Tetralone-Mediated Energy Transfer and 1,3-Hydrogen Shift
Organic Letters ( IF 4.9 ) Pub Date : 2024-03-18 , DOI: 10.1021/acs.orglett.4c00504
Yongbo Tan ₁ , Jing Zhao ₁ , Guo-Jun Deng _{1,

2} , Xiaochen Ji ₁ , Huawen Huang ₁

Affiliation

Herein, we introduce a tetralone-mediated photocyclization method of N-arylacrylamides. The protocol proceeds smoothly to deliver a diverse set of 3,4-dihydroquinolinones in moderate to good yields with excellent functional group compatibility and readily allows for late-stage modifications of a number of complex drug molecules. Mechanistic studies reveal that the present systems with ultraviolet light irradiation enable the cyclization via energy transfer and exclusive 1,3-hydrogen shift.

中文翻译：

通过四氢萘酮介导的能量转移和 1,3-氢转移从 N-芳基丙烯酰胺中获取 3,4-二氢喹啉酮

在此，我们介绍了一种四氢萘酮介导的N-芳基丙烯酰胺光环化方法。该方案进展顺利，以中等至良好的产率提供多种 3,4-二氢喹啉酮，具有出色的官能团相容性，并且易于对许多复杂药物分子进行后期修饰。机理研究表明，现有的紫外光照射系统能够通过能量转移和排他性的 1,3-氢转移实现环化。

更新日期：2024-03-18

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