6π 1,5-Diaza-electrocyclization of Isatin, α-Ketoester Derived Hydrazones with α,β-Unsaturated Ketoesters, Ketones, and Aldehydes Enables Functionalized Pyrazoles

A novel and efficient 6π 1,5-diaza-electrocyclization of readily available isatin, α-ketoester derived hydrazones with α,β-unsaturated ketoesters, ketones, and aldehydes has been developed. A series of functionalized pyrazoles bearing an oxindole unit were easily afforded by this tool with good yields and high functional group tolerance under mild conditions. Importantly, the obtained pyrazole could be further converted to 3-pyrazolecarboxylic acid with a quaternary carbon stereocenter.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-11-05
DOI
https://doi.org/10.1021/acs.joc.4c02070
Citations
2
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
0.50

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article

6π 1,5-Diaza-electrocyclization of Isatin, α-Ketoester Derived Hydrazones with α,β-Unsaturated Ketoesters, Ketones, and Aldehydes Enables Functionalized Pyrazoles

Mi Zhou, Liu Song
2 citations
The Journal of Organic Chemistry
Cyclopropane Reaction Mechanisms
0.50
article

6π 1,5-Diaza-electrocyclization of Isatin, α-Ketoester Derived Hydrazones with α,β-Unsaturated Ketoesters, Ketones, and Aldehydes Enables Functionalized Pyrazoles

Mi Zhou, Liu Song
article en
2 citations

Abstract

A novel and efficient 6π 1,5-diaza-electrocyclization of readily available isatin, α-ketoester derived hydrazones with α,β-unsaturated ketoesters, ketones, and aldehydes has been developed. A series of functionalized pyrazoles bearing an oxindole unit were easily afforded by this tool with good yields and high functional group tolerance under mild conditions. Importantly, the obtained pyrazole could be further converted to 3-pyrazolecarboxylic acid with a quaternary carbon stereocenter.

The Journal of Organic ChemistryVol. 89(22)
Chongqing University of Science and Technology (CN)
Chongqing Science and Technology Commission, Chongqing Municipal Education Commission, Chongqing University of Science and Technology
Clean water and sanitation
Openalex Percentile: Top 38%
Cyclopropane Reaction Mechanisms
0.50
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