Access to C5-Sulfonylated Tetrahydropyridazines via Photoinduced Cascade Sulfonylation-Cyclization of <i>N</i>-Cinnamyl Aldehyde Hydrazones
Direct installation of a sulfonyl functional group into the C5-position of tetrahydropyridazine was achieved using <i>N</i>'-benzylidene-<i>N</i>-cinnamylacetohydrazide as a new building skeleton via the photocatalytic carbosulfonylation/annulation procedure. Various substituted C5-sulfonylated tetrahydropyridazines were obtained in good to excellent yields employing aryl- or alkylsulfonyl chlorides as the sulfonyl radical sources. This reaction was realized through the selective addition of sulfonyl radical to the C2 position of cinnamyl followed by the 6<i>-endo-trig</i> annulation to the hydrazone CH═N bond.
Authors
- Changduo Pan (ORCID: https://orcid.org/0000-0001-5878-3835)
- Miao Zeng
Institutions
- Jiangsu University of Technology (CN)
- Clean Energy (United States) (US)
Publication Details
- Journal
- The Journal of Organic Chemistry
- Published
- 2025-04-15
- DOI
- https://doi.org/10.1021/acs.joc.5c00356
- Citations
- 2
- Primary Topic
- Sulfur-Based Synthesis Techniques
- Type
- article
- Field-Weighted Citation Impact
- 1.87
Funders
- Qinglan Project of Jiangsu Province of China
- Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology Department