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通过钯催化的级联分子内环化/分子间亲核加成反应简便合成喹啉取代的3-羟基-2-吲哚酮和3-氨基-2-吲哚酮

Facile Synthesis of Quinoline-Substituted 3-Hydroxy-2-oxindoles and 3-Amino-2-oxindoles via a Palladium-Catalyzed Cascade Intramolecular Cyclization/Intermolecular Nucleophilic Addition Reaction.

作者信息

Lin Huawei, Hu Xinyan, Han Bing, Yang Xianru, Deng Yiwei, Luo Jiayi, Ge Yanqing, Mao Biming, Wang Chang, Yuan Chunhao

机构信息

School of Chemistry and Pharmaceutical Engineering, Shandong First Medical University & Shandong Academy of Medical Sciences, Taian 271016, Shandong, P. R. China.

Pharmacy College, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117, Shandong, P. R. China.

出版信息

J Org Chem. 2024 Mar 1;89(5):3413-3418. doi: 10.1021/acs.joc.3c02837. Epub 2024 Feb 20.

DOI:10.1021/acs.joc.3c02837
PMID:38377573
Abstract

An efficient cascade intramolecular cyclization/intermolecular nucleophilic addition reaction of allenyl benzoxazinone with isatin or isatin-derived ketimine has been established by using Pd-π-Lewis base catalysis. A series of 3-hydroxy-2-oxindoles and 3-amino-2-oxindoles with quaternary carbon atoms at the C3 position were synthesized in good yields under mild conditions through this protocol.

摘要

通过钯-π-路易斯碱催化,建立了烯丙基苯并恶嗪酮与异吲哚酮或异吲哚酮衍生的酮亚胺的高效串联分子内环化/分子间亲核加成反应。通过该方法,在温和条件下以良好的产率合成了一系列在C3位带有季碳原子的3-羟基-2-吲哚酮和3-氨基-2-吲哚酮。

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