34648-00-5Relevant academic research and scientific papers
Synthesis of substituted 1-trifluoromethyl and 1-perfluoroalkyl-3- (arylamino)prop-2-en-1-one: Advances in the mechanism of Combes 2-trifluoromethyl and 2-perfluoroalkyl quinolines synthesis
El Kharrat, Salem,Laurent, Philippe,Blancou, Hubert
, p. 1252 - 1266 (2014/02/14)
We report a new synthesis and our study of the mechanism of formation of substituted 1-trifluoromethyl and 1-perfluoroalkyl-3-(phenylamino)prop-2-en-1- one starting from 3-(R-phenoxy)-3-perfluoroalkyl-prop-2-enals and arylamines. Reactivity study of the intermediates confirmed that 3-perfluoroalkyl-N, N′-diphenyl-1,5-diazapentadienes are the synthetic intermediates of the synthesis of 2-perfluoroalkylquinolines. The mechanism of the reaction of 1-trifluoromethyl and 1-perfluoroalkyl-3-(phenylamino)prop-2-en-1-one with POCl3 was studied. To our knowledge this is the first detection and isolation of N,N′-diaryldiazapentadiene derivatives as intermediates in the Combes F-alkyl substituted quinoline synthesis starting from enaminoketones. Finally, we succeeded isolating and identifying unsymmetrically substituted 2-perfluorolakyldiazapentadiene.
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 (2007/10/03)
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
How 2-anilinovinyl perfluoroalkyl ketones can be mechanistically correlated with their cyclization products 2-(perfluoroalkyl)quinolines
Schlosser, Manfred,Keller, Holger,Sumida, Shin-Ichi,Yang, Jin
, p. 8523 - 8526 (2007/10/03)
When heated in the presence of phosphoryl chloride, 2-anilinovinyl perfluoroalkyl ketones [e.g., 4-anilino-1,1,1-trifluorobut-3-en-2-one] afford 2-perfluoroalkyl)quinolines [e.g., 2-trifluoromethyl)quinoline. As revealed by cross-over experiments, an efficient amine exchange process randomizes the structural component in the final products but not in their aminoenone precursors. 1,3-Diaminoallyl cations (vinologous formidinium salts) are postulated to act as the turntables.
