1-（邻氨基苯基）2-丙炔醇和S/C亲核试剂的一锅接力Sc(III)/碱促进加成/环化：3-亚砜酰吲哚和3-芳酰吲哚衍生物的合成。

IF 3.3 2区化学 Q1 CHEMISTRY, ORGANIC

Journal of Organic Chemistry Pub Date : 2025-05-15 DOI:10.1021/acs.joc.5c00182

Chang He,Xiao-Han Qiu,Yi-Feng Lin,Ming Bian,Hui-Yu Chen,Yu-Ning Gao,Zhen-Jiang Liu

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引用次数: 0

摘要

建立了一种基于Sc(III)/碱促进的一锅接力Michael加成/环化/芳构化工艺的3-亚砜啉和3-芳基啉的高效合成策略。不同类型的亲核试剂（硫亲核试剂和碳亲核试剂）与1-（邻氨基苯基）2-醇原位生成的偶氮-炔基-邻醌类化合物（aza-o-AQMs）反应，以中等至优异的收率生成吲哚衍生物。该方法具有条件温和、起始材料简单、衬底范围广等优点。

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A One-Pot Relay Sc(III)/Base-Promoted Addition/Cyclization of 1-(o-Aminophenyl)prop-2-Ynols and S/C Nucleophiles: Synthesis of 3-Sulfenylindole and 3-Arylindole Derivatives.

An efficient strategy for the construction of 3-sulfenylindoles and 3-arylindoles based on a one-pot relay Sc(III)/base-promoted Michael addition/cyclization/aromatization process has been developed. Different types of nucleophiles (thio- and carbon nucleophiles) react with aza-alkynyl o-quinone methides (aza-o-AQMs) generated in situ from 1-(o-aminophenyl)prop-2-ynols to afford the indole derivatives in moderate to excellent yields. This method displays the advantages of mild conditions, simple starting materials, and broad substrate scope.

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来源期刊

Journal of Organic Chemistry 化学-有机化学

CiteScore

6.20

自引率

11.10%

发文量

1467

审稿时长

2 months

期刊介绍： Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.