512778-46-0Relevant academic research and scientific papers
2-(trifluoromethyl)quinolines from anilines: A novel mode of isomerization and cyclization
Keller,Schlosser
, p. 4637 - 4644 (1996)
Deprotonation of N-ethylidene-tert-butylamine with lithium diisopropylamide and subsequent condensation with ethyl trifluoroacetate gives 4-tert-butylamino-1,1,1-trifluorobut-3-en-2-one. An exchange of the amino substituent occurs when the latter compound
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.
