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Metal-free regioselective construction of 2-aryl-substituted quinolines via Aza-Henry (Nitro-Mannich) reactions under neat conditions
Synthetic Communications ( IF 1.8 ) Pub Date : 2020-09-01
Sandip Gangadhar Balwe, Jong Su Kim, Yeon Tae Jeong

A new and practical synthetic approach to construct 2-aryl-quinoline derivatives has been described through the sequential Aza-Henry (Nitro-Mannich) reaction using readily available 2,3-dihydro-1H-inden-5-amines, aldehydes and nitroalkanes under one-pot solvent-free reaction conditions using TsOH·H2O as the sustainable catalyst. In this regioselective approach, we described a cascade that proceeds through a sequential imine formation/Aza-Henry reaction/cyclization/denitration/rearrangement followed by oxidative aromatization to afford diverse 2-aryl-quinolines. This approach features large substrate scope, good functional group tolerance, mild reaction conditions and excellent yields with gram scale synthetic utility.



中文翻译:

在纯净条件下通过Aza-Henry(Nitro-Mannich)反应进行2芳基取代的喹啉的无金属区域选择性构建

通过使用易于获得的2,3-二氢-1 H-茚满-5-胺,醛和硝基烷烃进行的连续Aza-Henry(Nitro-Mannich)反应,已经描述了一种新型且实用的合成方法,用于构建2-芳基喹啉衍生物在使用TsOH·H 2 O作为可持续催化剂的一锅无溶剂反应条件下。在这种区域选择性方法中,我们描述了通过级联亚胺形成/ Aza-Henry反应/环化/脱硝/重排,然后进行氧化芳构化以提供各种2-芳基-喹啉而进行的级联反应。该方法具有较大的底物范围,良好的官能团耐受性,温和的反应条件以及具有克级合成效用的优异收率。

更新日期:2020-09-01
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