1860-46-4Relevant academic research and scientific papers
2-Position-Selective C-H Perfluoroalkylation of Quinoline Derivatives
Shirai, Takahiro,Kanai, Motomu,Kuninobu, Yoichiro
supporting information, p. 1593 - 1596 (2018/03/23)
We developed 2-position-selective, direct C-H trifluoromethylation, pentafluoroethylation, and heptafluoropropylation of quinoline derivatives. Regioselective transformation was achieved without derivatization of the quinolines. The reaction proceeded at room temperature with high functional group tolerance, even in gram scale. Notably, the reaction was applicable to substrates containing a functional group sensitive to oxidation and a drug molecule.
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.
New regiospecific synthesis of 2-trifluoromethyl-1,5 diazapentadiene compounds and of 2-trifluoromethylquinolines, their cyclization products
El Kharrat, Salem,Skander, Myriem,Dahmani, Abdelkader,Laurent, Philippe,Blancou, Hubert
, p. 8327 - 8331 (2007/10/03)
2-Trifluoromethylquinolines 5 are synthesized in high yields using a perfluoroalkylated gemiodoacetoxy derivative 3 and arylamines 4. The intermediate of this reaction, 2-trifluoromethyl-1,5-diazapentadiene compound 6, was isolated. The procedures are eas
3-Trifloxy-3-trifluoromethylpropeniminium triflate: Reaction with aromatic amines - An efficient synthesis of 2-trifluoromethylquinolines
Baraznenok, Ivan L.,Nenajdenko, Valentine G.,Balenkova, Elizabeth S.
, p. 937 - 941 (2007/10/03)
The reaction of iminium triflates 2 and 7 with various aromatic amines were investigated. The 2-R(f)-substituted quinolines 3 and 8 were prepared in excellent yields by the reaction of 2 and 7, respectively, with substituted anilines. The reactions of 2 a
2-(trifluoromethyl)quinolines from anilines: A novel mode of isomerization and cyclization
Keller,Schlosser
, p. 4637 - 4644 (2007/10/03)
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
