Synthesis of 1-Thio-Substituted Isoquinoline Derivatives by Tandem Cyclization of Isothiocyanates

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• 作者：Li-Rong Wen ; Qian Dou ; Yuan-Chao Wang ; Jin-Wei Zhang ; Wei-Si Guo ; Ming Li
• 刊名：Journal of Organic Chemistry
• 出版年：2017
• 出版时间：February 3, 2017
• 年：2017
• 卷：82
• 期：3
• 页码：1428-1436
• 全文大小：530K
• ISSN：1520-6904

文摘

A copper-catalyzed tandem arylation–cyclization process to access 1-(arylthio)isoquinolines from isothiocyanates and diaryliodonium salts is described. It is the first general method to construct the potentially useful 1-(arylthio)isoquinoline derivatives. Moreover, 1-(methylthio)isoquinoline derivatives were also achieved successfully with MeOTf instead of diaryliodonium salts under metal-free conditions. Mechanistic studies reveal that these two processes proceed in different routes. This method has been successfully applied to the synthesis of quinazolinone alkaloid rutaecarpine.