Synthesis of 8-Aminoquinolines by Using Carbamate Reagents: Facile Installation and Deprotection of Practical Amidating Groups
Synthesis of 8-Aminoquinolines by Using Carbamate Reagents: Facile Installation and Deprotection of Practical Amidating Groups
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DOI：
10.1002/chem.201503511
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发表时间：
2015-11-23
影响因子：
4.3
通讯作者：
Chang, Sukbok
中科院分区：
文献类型：
--
作者：
Gwon, Donghyeon;Hwang, Heejun;Chang, Sukbok
本文描述了通过使用易于安装和易于脱保护的酰胺化试剂来开发8-氨基喹啉的实用路线。在RhIII催化的条件下优化了两个可扩展的程序：i）使用预生成的氯代氨基甲酸酯和ii）直接使用氨基甲酸酯的两步一锅法。这两种方法都非常方便，在温和的条件下合成8-氨基喹啉的克规模。在Pd催化的转移氢化条件下，实现了合成的通用酰胺化基团的容易脱保护，同时喹啉N-氧化物的脱氧，从而以优异的总体效率产生8-氨基喹啉。
Described herein is the development of practical routes to 8-aminoquinolines by using readily installable and easily deprotectable amidating reagents. Two scalable procedures were optimized under RhIII-catalyzed conditions: i) the use of pre-generated chlorocarbamates and ii) a two-step one-pot process that directly employs carbamates. Both approaches are highly convenient for the gram-scale synthesis of 8-aminoquinolines under mild conditions. Facile deprotection of the synthetically versatile amidating groups was achieved under the Pd-catalyzed transfer hydrogenation conditions with simultaneous deoxygenation of quinoline N-oxides, thus yielding 8-aminoquinolines in excellent overall efficiency.