Metal-Free Synthesis of 3-Arylquinolin-2-ones from Acrylic Amides via a Highly Regioselective 1,2-Aryl Migration: An Experimental and Computational Study

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• 作者：Le Liu ; Tonghuan Zhang ; Yun-Fang Yang ; Daisy Zhang-Negrerie ; Xinhao Zhang ; Yunfei Du ; Yun-Dong Wu ; Kang Zhao
• 刊名：Journal of Organic Chemistry
• 出版年：2016
• 出版时间：May 20, 2016
• 年：2016
• 卷：81
• 期：10
• 页码：4058-4065
• 全文大小：508K
• 年卷期：0
• ISSN：1520-6904

文摘

Combined experimental and theoretical investigations into the phenyliodine bis(trifluoroacetate) (PIFA)-mediated reaction of N-arylcinnamamide to produce 3-arylquinolin-2-one derivatives have been conducted. High regioselectivity during the aryl migration process was observed in 3,3-disubstituted acrylamides. Density functional theory calculation was conducted in an attempt to understand the mechanism and the origin of the regioselectivity. On the basis of both the experimental and the theoretical results, a mechanism involving an oxidative annulation, followed by an aryl migration, has been proposed. The annulation is the regioselectivity determining step.