PyBroP/base-promoted one-pot three-component sequential decarboxylative addition reaction of β-keto acids, isatylidene malononitriles and pyridine <i>N</i> -oxides

A PyBroP/base-promoted three-component sequential decarboxylative nucleophilic addition protocol has been developed. Under the optimized conditions, a wide array of β-keto acids, isatylidene malononitriles and pyridine <i>N</i>-oxides couple efficiently to deliver the desired 3,3-disubstituted oxindole-fused pyridine derivatives in moderate to excellent yields. This method features good functional group tolerance, high positional selectivity, mild reaction conditions, and a one-pot procedure. The methodology can be scaled up to the gram scale, and the synthetic utility of the product was further validated. Control experiments have also been carried out to elucidate the plausible mechanistic pathway.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2026-01-01
DOI
https://doi.org/10.1039/d5ob01772f
Primary Topic
Multicomponent Synthesis of Heterocycles
Type
article
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article

PyBroP/base-promoted one-pot three-component sequential decarboxylative addition reaction of β-keto acids, isatylidene malononitriles and pyridine N -oxides

Fuzhong Han, Xiang‐Ping Hu, Lina Jia, Yingdong Na
Organic & Biomolecular Chemistry
Multicomponent Synthesis of Heterocycles
article

PyBroP/base-promoted one-pot three-component sequential decarboxylative addition reaction of β-keto acids, isatylidene malononitriles and pyridine N -oxides

Fuzhong Han, Xiang‐Ping Hu, Lina Jia, Yingdong Na
article en

Abstract

A PyBroP/base-promoted three-component sequential decarboxylative nucleophilic addition protocol has been developed. Under the optimized conditions, a wide array of β-keto acids, isatylidene malononitriles and pyridine <i>N</i>-oxides couple efficiently to deliver the desired 3,3-disubstituted oxindole-fused pyridine derivatives in moderate to excellent yields. This method features good functional group tolerance, high positional selectivity, mild reaction conditions, and a one-pot procedure. The methodology can be scaled up to the gram scale, and the synthetic utility of the product was further validated. Control experiments have also been carried out to elucidate the plausible mechanistic pathway.

Organic & Biomolecular ChemistryVol. 24(5)
Qiqihar University (CN), Dalian Institute of Chemical Physics (CN), Chinese Academy of Sciences (CN)
Openalex Percentile: Top 96%
Multicomponent Synthesis of Heterocycles
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PyBroP/base-promoted one-pot three-component sequential decarboxylative addition reaction of β-keto acids, isatylidene malononitriles and pyridine <i>N</i> -oxides — Fuzhong Han, Xiang‐Ping Hu, et al. · Organic & Biomolecular Chemistry (2026) | TGRS Research Map | TGRS