Metal-Free Reaction of ortho-Carbonylated Alkynyl-Substituted Arylaldehydes with Common Amines: Selective Access to Functionalized Isoindolinone and Indenamine Derivatives

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• 作者：Dr. Ziping Cao ; Hongbo Zhu ; Dr. Xin Meng ; Jun Guan ; Qiang Zhang ; Laijin Tian ; Xuejun Sun ; Guang Chen and Prof. Dr. Jinmao You
• 刊名：Chemistry - A European Journal
• 出版年：2016
• 出版时间：November 14, 2016
• 年：2016
• 卷：22
• 期：47
• 页码：16979-16985
• 全文大小：674K
• ISSN：1521-3765

文摘

Herein we describe a reaction of ortho-carbonylated alkynyl-substituted arylaldehydes with common primary amines that can provide functionalized isoindolinone and 3-hydroxylindenamine products in high yields. Depending on the substituent size of primary amines, two distinct reaction pathways were exploited selectively, that are, an initial aza-conjugate addition followed by hydrogen transfer to access isoindolinone framework and a unique oxa-conjugate addition followed by Petasis–Ferrier rearrangement to afford indenamine derivatives. In the presence of Et₃N, the reaction property of small primary amines was changed, proceeding to afford 3-hydroxylindenamine derivatives efficiently. These products contain interesting substructures that exist in many natural products and bioactive molecules. The reaction features contain the use of transition-metal-free catalysts, simple operation, broad substrate scope, and product diversity.