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Metal-Free Synthesis of 2-Substituted 3-(2-Hydroxyaryl)quinolines and 4-(2-Hydroxyaryl)acridines via Benzyne Chemistry
The Journal of Organic Chemistry ( IF 3.6 ) Pub Date : 2017-11-15 00:00:00 , DOI: 10.1021/acs.joc.7b02149
Ankit Kumar Dhiman 1 , Rakesh Kumar 1 , Rakesh Kumar 1 , Upendra Sharma 1
Affiliation  

A metal-free approach for the synthesis of 3-aryl-2-substituted quinolines and 4-arylacridines has been developed via the 1,3-dipolar cycloaddition reactions of arynes with N-oxides. Reactions of various 2-substitued quinoline N-oxides with ortho-(trimethylsilyl)aryltriflates in the presence of KF gave 3-(2-hydroxyaryl)quinoline derivatives in good yields. Acridine N-oxides also reacted with arynes to furnish 4-(2-hydroxyaryl)acridines, albeit in moderate yields.

中文翻译:

通过苯炔化学无金属合成2-取代的3-(2-羟基芳基)喹啉和4-(2-羟基芳基)ac啶

通过芳烃与N-氧化物的1,3-偶极环加成反应,已经开发出一种无金属的方法来合成3-芳基-2-取代的喹啉和4-芳基吡啶。在KF存在下,各种2-取代的喹啉N-氧化物与-(三甲基甲硅烷基)芳基三氟甲磺酸的反应以良好的产率得到了3-(2-羟基芳基)喹啉衍生物。cr啶N-氧化物也与芳烃反应生成4-(2-羟基芳基)ac啶,尽管产率中等。
更新日期:2017-11-16
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