Electrochemical Oxidation Ring-Opening of Spiro-Dihydroheteroaromatics with <i>N</i> -(Arylsulfonyl)acrylamides to Form Quinazolinone-Containing Long-Chain Amides

An electrochemically driven cascade oxidative reaction was developed using spiro-dihydroquinazolinones and activated alkenes, involving N-centered radical cation-induced C-C bond cleavage, C-C bond formation, and subsequent Truce-Smiles rearrangement. This aromatic-driven deconstruction functionalization strategy efficiently generates valuable long-chain amides containing quinazolinones with α-full-carbon tetrahedral centers. This protocol features mild reaction conditions, good functional group compatibility, and high reaction efficiency for achieving bifunctionalization of activated alkenes.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-04-22
DOI
https://doi.org/10.1021/acs.joc.5c02915
Primary Topic
Quinazolinone synthesis and applications
Type
article
Field-Weighted Citation Impact
0.00

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article

Electrochemical Oxidation Ring-Opening of Spiro-Dihydroheteroaromatics with N -(Arylsulfonyl)acrylamides to Form Quinazolinone-Containing Long-Chain Amides

Yiran Zhao, Yuyu Dai, Xinyu Lü, Xiangsheng Xu et al.
The Journal of Organic Chemistry
Quinazolinone synthesis and applications
article

Electrochemical Oxidation Ring-Opening of Spiro-Dihydroheteroaromatics with N -(Arylsulfonyl)acrylamides to Form Quinazolinone-Containing Long-Chain Amides

Yiran Zhao, Yuyu Dai, Xinyu Lü, Xiangsheng Xu, Jiarui Sun, Xiangyu Mou
article en

Abstract

An electrochemically driven cascade oxidative reaction was developed using spiro-dihydroquinazolinones and activated alkenes, involving N-centered radical cation-induced C-C bond cleavage, C-C bond formation, and subsequent Truce-Smiles rearrangement. This aromatic-driven deconstruction functionalization strategy efficiently generates valuable long-chain amides containing quinazolinones with α-full-carbon tetrahedral centers. This protocol features mild reaction conditions, good functional group compatibility, and high reaction efficiency for achieving bifunctionalization of activated alkenes.

The Journal of Organic ChemistryVol. 91(18)
Zhejiang University of Technology (CN)
National Natural Science Foundation of China, Natural Science Foundation of Zhejiang Province
Clean water and sanitation
Openalex Percentile: Top 22%
Quinazolinone synthesis and applications
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