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

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.…”

“…To do this we have focused our attention on β-aminovinyl trifluoromethyl ketones, which are frequently exploited as valuable starting compounds in the preparation of various trifluoromethylated aromatic and heterocycle molecules. [21][22][23] Organic functionalities with specific properties that we are interested in can in principle be at-tached at four positions of the enaminone using readily available starting materials and different synthetic strategies. [13][14][15] β-Aminovinyl ketones with a fluoroalkyl moiety are thus considered to be interesting building blocks that can be decorated in a number of synthetic sequences to produce diverse molecular entities for specifically designed applications.…”

“…Their potential for diverse coordination chemistry27–36 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. Moreover, these enaminone building blocks offer great potential for rapidly generating molecular diversity (see the general structure in Scheme ) because these organic substrates can be structurally modified at different sites (R 1 , R 2 , R 3 and R 4 ) by variation of 1) the amine (R 1 ), 2) the substitution on the C=C double bond (R 2 and R 3 ) and 3) the fluoroalkyl moiety (R 4 ) 21–23. Organic functionalities with specific properties that we are interested in can in principle be attached at four positions of the enaminone using readily available starting materials and different synthetic strategies.…”

Synthesis of 2,3-Dihydro-4-pyridones and 4-Pyridones by the Cyclization Reaction of Ester-Tethered Enaminones

“…However, structure 1 is less common. A few examples involve N -trimethylsilyloxy derivatives (R = Me 3 SiO) obtained by silylation of β-substituted aliphatic nitro compounds, N-heteroaryl derivatives formed by the reaction of annelated 2-aminothiophene with methyl propiolate in refluxing toluene, bis­(chlorodifluoromethyl)­keto derivatives (ClF 2 CO instead of CO 2 Et in 1 ) formed by the self condenzation of the corresponding enamino ketone under basic conditions, and mixed keto–ester derivatives obtained by the reaction of enamino ketone with ethyl propiolate in the presence of a base. , This unsymmetrical dialkenyl amine could rearrange to polysubstituted conjugated dienes or afford spirooxindoles upon treatment with isatin . Obviously, the synthetic potential of structure 1 has yet to be disclosed.…”

Synthesis of fluorofurans and perfluoroalkylfurans

“…The transformation proceeds in THF in 95% yield [178]. One of the methods of furyldifluoroethanol synthesis is based on the reaction of furfural with difluoroenamines in the presence of Lewis acids (Scheme 73) [179].…”