Visible-Light-Induced C–H Alkylation of 1,2,4-Triazine-3,5(2<i>H</i>,4<i>H</i>)-diones via Infrequent 1,2-Hydrogen-Atom Transfer
1,2,4-Triazine-3,5(2<i>H</i>,4<i>H)</i>-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(2<i>H</i>,4<i>H</i>)-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(2<i>H</i>,4<i>H</i>)-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(sp<sup>2</sup>)-C(sp<sup>3</sup>) bonds via infrequent 1,2-HAT under current conditions.
Authors
- Li Guo (ORCID: https://orcid.org/0000-0002-7445-5257)
- Guanghui Lv (ORCID: https://orcid.org/0000-0003-4846-9564)
- Yong Wu (ORCID: https://orcid.org/0000-0003-0719-4963)
- Cuimei Zhang (ORCID: https://orcid.org/0000-0002-3682-1834)
- Yangyang Wang (ORCID: https://orcid.org/0000-0003-2255-6141)
- Jie Wang (ORCID: https://orcid.org/0009-0006-0016-1324)
- Mi Wang (ORCID: https://orcid.org/0000-0003-2799-5987)
- Jian Chen (ORCID: https://orcid.org/0000-0001-5128-8567)
- Yafei Zhu (ORCID: https://orcid.org/0009-0000-1002-0708)
- Penghua Zhang
Institutions
- Hubei University of Medicine (CN)
- Sichuan University (CN)
- Taihe Hospital (CN)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-05-19
- DOI
- https://doi.org/10.1021/acs.joc.5c00635
- Citations
- 8
- Primary Topic
- Radical Photochemical Reactions
- Type
- article
- Field-Weighted Citation Impact
- 7.49
Funders
- Sichuan Province Science and Technology Support Program