Assembly of 1,3-diaryl-1<i>H</i>-pyrazoles <i>via</i> base-mediated [3 + 2] cycloaddition

1,3-Diaryl-1<i>H</i>-pyrazoles, serving as privileged heterocyclic scaffolds, demonstrate significant application potential in pharmaceutical development, functional materials, and agrochemical industries. This study presents a synthetic strategy based on [3 + 2] cycloaddition, achieving efficient construction of 1,3-diaryl-1<i>H</i>-pyrazoles. A novel transition metal-free protocol was established through base-catalyzed intermolecular annulation of hydrazones with vinyl sulfoxides, followed by oxidation. The reaction system exhibited excellent substrate generality and demonstrated successful gram-scale synthesis. Subsequent investigations into synthetic applications further confirmed the methodology's practicality and scalability.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob00907c
Citations
1
Primary Topic
Synthesis and Reactions of Organic Compounds
Type
article
Field-Weighted Citation Impact
0.94

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article

Assembly of 1,3-diaryl-1H-pyrazoles via base-mediated [3 + 2] cycloaddition

Tenglong Xu, Ai‐Fang Wang, Min Wang, Jian Yan et al.
1 citations
Organic & Biomolecular Chemistry
Synthesis and Reactions of Organic Compounds
0.94
article

Assembly of 1,3-diaryl-1H-pyrazoles via base-mediated [3 + 2] cycloaddition

Tenglong Xu, Ai‐Fang Wang, Min Wang, Jian Yan, Yi Chen, Zimei Zhong
article en
1 citations

Abstract

1,3-Diaryl-1<i>H</i>-pyrazoles, serving as privileged heterocyclic scaffolds, demonstrate significant application potential in pharmaceutical development, functional materials, and agrochemical industries. This study presents a synthetic strategy based on [3 + 2] cycloaddition, achieving efficient construction of 1,3-diaryl-1<i>H</i>-pyrazoles. A novel transition metal-free protocol was established through base-catalyzed intermolecular annulation of hydrazones with vinyl sulfoxides, followed by oxidation. The reaction system exhibited excellent substrate generality and demonstrated successful gram-scale synthesis. Subsequent investigations into synthetic applications further confirmed the methodology's practicality and scalability.

Organic & Biomolecular ChemistryVol. 23(31)
Hangzhou Normal University (CN)
National Natural Science Foundation of China
Openalex Percentile: Top 24%
Synthesis and Reactions of Organic Compounds
0.94
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Assembly of 1,3-diaryl-1<i>H</i>-pyrazoles <i>via</i> base-mediated [3 + 2] cycloaddition — Tenglong Xu, Ai‐Fang Wang, et al. · Organic & Biomolecular Chemistry (2025) | TGRS Research Map | TGRS