1439401-87-2Relevant academic research and scientific papers
Metal-Free Synthesis of 3-Arylquinolin-2-ones from Acrylic Amides via a Highly Regioselective 1,2-Aryl Migration: An Experimental and Computational Study
Liu, Le,Zhang, Tonghuan,Yang, Yun-Fang,Zhang-Negrerie, Daisy,Zhang, Xinhao,Du, Yunfei,Wu, Yun-Dong,Zhao, Kang
, p. 4058 - 4065 (2016/06/08)
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.
PhI(OCOCF3)2-mediated C-C bond formation concomitant with a 1,2-Aryl shift in a metal-free synthesis of 3-arylquinolin-2-ones
Liu, Le,Lu, Hang,Wang, Hong,Yang, Chao,Zhang, Xiang,Zhang-Negrerie, Daisy,Du, Yunfei,Zhao, Kang
, p. 2906 - 2909 (2013/07/26)
The reaction of the readily available N-methyl-N-phenylcinnamamides with phenyliodine bis(trifluoroacetate) (PIFA) in the presence of Lewis acids provides a general and efficient assembly of a variety of 3-arylquinolin-2-one compounds. This novel approach features not only metal-free oxidative C(sp 2)-C(sp2) bond formation but also an exclusive 1,2-aryl migration.
