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.
Authors
- Yiran Zhao (ORCID: https://orcid.org/0000-0002-0841-967X)
- Yuyu Dai (ORCID: https://orcid.org/0000-0002-3621-783X)
- Xinyu Lü (ORCID: https://orcid.org/0000-0003-4619-0850)
- Xiangsheng Xu (ORCID: https://orcid.org/0000-0002-4475-3720)
- Jiarui Sun
- Xiangyu Mou
Institutions
- Zhejiang University of Technology (CN)
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
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Zhejiang Province