2- Arylquinolines, formation

Some routes have been described which involve the formation of two C-C bonds in the same pot to produce quinolines and isoquinolines. For the production of 2-arylquinolines a Schiff base is reacted with an enol ether in presence of ytterbium(III) triflate. 2-Chloro-3-formylquinolines result from a practically simple process... 

The reaction of Al-methyl-Al-phenylcinnamamides with phenyliodine bis (trifluoroacetate) in the presence of Lewis acids provides 3-arylquinolin-2-ones and involves a metal-free oxidative C(sp )-C sp ) bond formation and a 1,2-aryl migration (Scheme 89). " ... 

Zhao et al. utilized the remarkable oxidative property of FIFA in a C-C bond formation to prepare an array of 3-arylquinolin-2-ones 120 (Scheme 26). FIFA-promoted oxidation of N-methyl-N-phenylcinnamamides 119 in the presence of a Lewis acid afforded 3-arylquinolin-2-ones in good yields. Formation of 3-arylquinolin-2-ones was realized through the FIFA-promoted simultaneous C-C bond formation and 1,2-aryl migration. This simple and metal-free FIFA-mediated green approach for the biologically important 3-arylquinolin-2-ones also widen the synthetic utility of hypervalent iodine reagents [42]. 

L. Liu, H. Lu, H. Wang, C. Yang, X. Zhang, D. Zhang-Negrerie, Y. Du, K. Zhao, 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, Org. Lett. 15 (2013) 2906-2909. 

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