Synthesis of novel fluorinated 4-aminoquinoline derivatives

Bidentate and Tetradentate β‐Aminovinyl Trifluoromethylated Ketones and Their Copper(II) Complexes: Synthesis, Characterization and Redox Chemistry

“…These organic substrates can be structurally modified at different sites (R 1 , R 2 , R 3 and R 4 ), by variation of the amine (R 1 ), the substitution on the C=C bond (R 2 and R 3 ) and at the fluoroalkyl moiety (R 4 ). [14][15][16][17][18][19][20] In principle, organic functionalities with specific properties can be attached at the four positions of the enaminone from readily available starting materials using different synthetic strategies. The fluorine atoms are significant as they may induce specific interactions in the solid state such as F···H, F···F, F···O=C, F···N and F···S contacts; these properties have been used with success in materials science and crystal engineering, [30][31] in medicinal chemistry in order to design more active drug candidates and have been exemplified by cocrystallized structures of potent therapeutic agents with target enzymes.…”

Copper(II) Cubane Complexes Built from Electro‐ and Photosensitive β‐Aminovinyl Trifluoromethyl Ketone Ligands

“…Our research is currently devoted to the elaboration of ligands able to bring additional properties to the magnetic core with the expectation that both properties could interact cooperatively. [8,[16][17][18][19][20][21][22][23][24][25][26] Their potential for diverse coordination chemistry [27][28][29][30][31][32][33][34][35][36] combined with appropriate pendant organic functionalities (a photosensitive unit, a stable radical, an electron donor, a luminescent unit or a biomolecule) make them attractive for the design of new generations of original materials. [8] On the other hand, their ability to coordinate a large panel of transition-metal ions have led to the preparation of a number of metallomesogens with interesting liquid-crystal properties [9][10][11][12] or highly-active catalysts for olefin polymerization, including fluorinated enaminones.…”

Indium-mediated reduction of β-aminovinyl chloro-difluoromethylated ketones in the presence of heteroaryl aldehydes

“…) in anhydrous DMF (À30 8C to room temperature over 3 h). Substrate 1h was prepared by adding tryptamine to crude 1-chloro-4,4-diethoxy-1,1-difluorobuten-3-en-2-one [10] and was obtained in a 30% isolated yield (not optimized, Scheme 3). The free NH substrates 1a-g were obtained as Z isomers (and E isomer for 1h), as determined by 1 H NMR (small coupling constant of the olefinic protons of 6-8 Hz and a deshielded peak of the amino proton d H > 10.0 ppm) due to hydrogen bonding between NH and C O.…”

“…Other free NH enaminones 1d (entry 5), 1e (entries 6 and 7), 1f (entry 9) gave usually good yields of alcohols, with good conversions with the exception of reaction of 1e with 3,4-dimethoxyphenyl benzaldehyde (entry 8) and 1h with benzaldehyde (entry 11). Alcohol adduct 3ga (entry 10), resulting from the coupling reaction of 1g and benzaldehyde needed 2 equiv. of indium but was too unstable to be isolated by silica gel chromatography.…”

“…13 C NMR (DMSO-d 6 ): d 188.1 (dd, J = 28.3, 25.5, C-2, Z or E), 186.6 (dd, J = 28.1, 25.1, C-2, Z or E), 148.3 (C-4, Z or E), 146.1 (C-4, Z or E), 139.6 (C-5, Z or E), 138.7 (C-5, Z or E), 137.8 (C- 10), 129.7 (C-6), 128.3 (C- 11), 128.0 (C- 12), 128.0 (C-13), 127.3 (C-8), 118.9 (C-7, Z or E), 117.9 (C-7, Z or E), 117.0 (dd, J = 261.2, 252.6, C-1), 96.1 (C-3, Z or E), 92.4 (C-3, Z or E), 71.9 (dd, J = 28. 6, 23.7, C-9).…”