C鈥揌 Activation Guided by Aromatic N鈥揌 Ketimines: Synthesis of Functionalized Isoquinolines Using Benzyl Azides and Alkynes

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• 作者：Sreya Gupta ; Junghoon Han ; Yongjin Kim ; Soon W. Lee ; Young Ho Rhee ; Jaiwook Park
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：October 3, 2014
• 年：2014
• 卷：79
• 期：19
• 页码：9094-9103
• 全文大小：630K
• ISSN：1520-6904

文摘

Aromatic N鈥揌 ketimines were in situ generated from various benzylic azides by ruthenium catalysis for the subsequent Rh-catalyzed annulation reaction with alkynes to give the corresponding isoquinolines. In contrast to conventional synthetic methods for aromatic N鈥揌 ketimines, our protocol works under mild and neutral conditions, which enabled the synthesis of isoquinolines having various functionalities such as carbonyl, ester, alkenyl, and ether groups. In addition, the imidates generated from 伪-azido ethers were successfully used for the synthesis of 1-alkoxyisoquinolines.