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.

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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

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article

Access to C5-Sulfonylated Tetrahydropyridazines via Photoinduced Cascade Sulfonylation-Cyclization of N-Cinnamyl Aldehyde Hydrazones

Changduo Pan, Miao Zeng
2 citations
The Journal of Organic Chemistry
Sulfur-Based Synthesis Techniques
1.87
article

Access to C5-Sulfonylated Tetrahydropyridazines via Photoinduced Cascade Sulfonylation-Cyclization of N-Cinnamyl Aldehyde Hydrazones

Changduo Pan, Miao Zeng
article en
2 citations

Abstract

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.

The Journal of Organic ChemistryVol. 90(16)
Jiangsu University of Technology (CN), Clean Energy (United States) (US)
Qinglan Project of Jiangsu Province of China, Jiangsu Key Laboratory of Advanced Catalytic Materials and Technology Department
Clean water and sanitation
Openalex Percentile: Top 16%
Sulfur-Based Synthesis Techniques
1.87
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