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在微波辐射下,以六甲基二硅氮烷为氮源,通过环境友好的Nafion催化合成3-取代异喹啉。

Environmentally friendly Nafion-catalyzed synthesis of 3-substituted isoquinoline by using hexamethyldisilazane as a nitrogen source under microwave irradiation.

作者信息

Lin Tzu-Chun, Chan Chieh-Kai, Chung Yi-Hsiu, Wang Cheng-Chung

机构信息

Institute of Chemistry, Academia Sinica, Taipei 115, Taiwan.

出版信息

Org Biomol Chem. 2023 Sep 20;21(36):7316-7326. doi: 10.1039/d3ob01032e.

Abstract

This study developed an eco-friendly method to synthesize 3-arylisoquinoline from 2-alkynylbenzaldehydes using Nafion® NR50 as an acidic catalyst and hexamethyldisilazane (HMDS) as a nitrogen source. The reaction proceeded a 6- cyclization under microwave irradiation, giving the corresponding isoquinolines in excellent yields. The advantages of this protocol include: (1) the use of recyclable acid catalysts, (2) transition-metal-free catalysis, and (3) the effective formation of the target product. These features make this methodology a promising approach for the sustainable and efficient synthesis of 3-arylisoquinoline. Some structures were also confirmed by single-crystal X-ray diffraction analysis.

摘要

本研究开发了一种环保方法,以Nafion® NR50为酸性催化剂、六甲基二硅氮烷(HMDS)为氮源,从2-炔基苯甲醛合成3-芳基异喹啉。该反应在微波辐射下进行6-环化反应,以优异的产率得到相应的异喹啉。该方法的优点包括:(1)使用可回收的酸催化剂;(2)无过渡金属催化;(3)有效形成目标产物。这些特点使该方法成为可持续高效合成3-芳基异喹啉的一种有前景的方法。一些结构也通过单晶X射线衍射分析得到证实。

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