794574-59-7Relevant academic research and scientific papers
The reaction of 2-fluoroalkyl-1-iodoethylenes with arylamines: A facile method for the synthesis of fluoroalkylated quinolines and enaminoketones
Zhao, Fulu,Yang, Xianjin,Liu, Jintao
, p. 9945 - 9951 (2004)
The reaction of 2-fluoroalkyl-1-iodoethylenes with arylamines (1) and the subsequent acid promoted transformation of the products were described. In the presence of ZnCl2 and triethylamine, 1 reacted readily with various p-substituted anilines in HMPA under a vacuum of 60-70 mmHg to give the corresponding enaminoaldehydes (2) as a mixture of E- and Z-isomers. Cyclization of 2, without further purification in refluxing toluene, catalyzed by strong acids such as p-toluene sulfonic acid and trifluoromethanesulfonic acid gave 2-fluoroalkylquinolines (3) in good yields, while fluoroalkylated enaminoketones (4) were obtained predominantly when 2 was treated with acids in aqueous THF solution. A possible mechanism was proposed for the formation of 3 and 4. Graphical Abstract
