可见光诱导1,2,4-三嗪-3,5(2H,4H)-二酮的C-H烷基化

IF 3.6 2区 化学 Q1 CHEMISTRY, ORGANIC
Mi Wang, Yangyang Wang, Jie Wang, Yafei Zhu, Penghua Zhang, Cuimei Zhang, Jian Chen, Li Guo*, Guanghui Lv* and Yong Wu*, 
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引用次数: 0

摘要

1,2,4-三嗪-3,5(2H,4H)-二酮广泛存在于各种药物分子和生物活性分子中。首次报道了一种通过酰胺自由基1,2-氢原子转移(1,2- hat)的可见光驱动1,2,4-三嗪-3,5(2H,4H)-二酮的C-H烷基化反应,为丰富1,2,4-三嗪-3,5(2H,4H)-二酮的结构和功能多样性提供了一种环保和可持续的途径。该新工艺具有反应温和、无金属、操作简单、官能团耐受性好等特点。令我们高兴的是,在目前的条件下,其他杂环化合物,如异喹啉和香豆素,也会通过罕见的1,2- hat进行烷基化反应,形成C(sp2)-C(sp3)键。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Visible-Light-Induced C–H Alkylation of 1,2,4-Triazine-3,5(2H,4H)-diones via Infrequent 1,2-Hydrogen-Atom Transfer

Visible-Light-Induced C–H Alkylation of 1,2,4-Triazine-3,5(2H,4H)-diones via Infrequent 1,2-Hydrogen-Atom Transfer

1,2,4-Triazine-3,5(2H,4H)-diones are widely present in various drug molecules and bioactive molecules. A visible-light-driven C–H alkylation of 1,2,4-triazine-3,5(2H,4H)-diones via 1,2-hydrogen-atom transfer (1,2-HAT) of amide radicals is first reported, providing an environmentally friendly and sustainable pathway to enrich the structural and functional diversity of 1,2,4-triazine-3,5(2H,4H)-diones. This novel protocol is characterized by mild and metal-free reaction conditions, an operationally simple method, and good functional group tolerance. To our delight, other heterocycles, such as isoquinoline and coumarin, also undergo alkylation reactions to construct C(sp2)-C(sp3) bonds via infrequent 1,2-HAT under current conditions.

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来源期刊
Journal of Organic Chemistry
Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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