An efficient method for the synthesis of β-enaminones and β-enaminoesters using a combination of [(PPh3)AuCl]/AgOTf as catalyst has been developed. The reaction between 1,3-dicarbonyl compounds and primary amines was carried out under solvent-free co...
An efficient method has been developed for the synthesis of β-enaminones under solvent-free reaction conditions using PPA-SiO2 as catalyst. The reaction yields were good to excellent (up to 90%). This methodology affords high selectivity and good tol...
A controllable synthesis of trisubstituted imidazoles and pyrroles has been developed through rhodium(II)-catalyzed regioselective annulation of N-sulfonyl-1,2,3-trizaoles with β-enaminones. The imidazole ring was formed through a 1,1-insertion...
The reaction of isodehydracetic acid with amines was serendipitously found to afford β-enaminones in the presence of the coupling agent 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride (EDC). Under the optimal reaction condition, 23 examp...
One-pot synthesis of three enaminones, (E)-1-(4-chlorophenyl)-3-morpholinoprop-2-en-1-one 1, (E)-1-(4-chlorophenyl)-3-(4-methylpiperazin-1-yl)prop-2-en-1-one 2, and (E)-1-(4-chlorophenyl)-3-(pyrrolidin-1-yl)prop-2-en-1-one 3 were achieved. The synthe...
In the search for new potential drug candidates acting as anticancer agents, we were interested in a small molecule derived from 4-hydroxy-2-quinolone, which is newly synthesized from the condensation of a β-enaminone and diethylmalonate under m...
The fortuitous modification of a quinoline-proline-piperazine side chain linked to a steroid in the presence of lithium (trimethylsilyl) acetylide has generated an unknown product that is more active than its precursor. After having characterized two...
(E)-1-(1H-Benzo[d]imidazol-2-yl)-3-(dimethylamino)prop-2-en-1-one 2 was synthesized by one-pot synthesis protocol of 2-acetyl benzo[d]imidazole with dimethylformamide dimethylacetal (DMF-DMA) in xylene at 140 °C for 8 h. Reaction of enaminone der...
Enaminones are chemical compounds incorporating an amino group linked through a C=C to carbonyl group.[...]
Organic compounds with 1,3-diketone or 3-amino enone functional groups are extremely important as they can be converted into a plethora of carbo- or heterocyclic derivatives or can be used as ligands in the formation of metal complexes. Here, we have...
2-Methyl-4-oxo-4,5-dihydro-1H-pyrrole-3-carboxylic acid phenylamide was obtained as a single product in an experiment on the cyclization modes of a glycine-derived enamino amide. High yield and operational simplicity are the main features of the pres...
A novel, eco-friendly, and efficient method for constructing 2,3-disubstituted chromone skeletons from readily available water, o-hydroxyaryl enaminones (o-HPEs), and aryldiazonium salts has been developed under mild reaction conditions. This α...
A series of differently substituted β-enaminones 2a,b, 4a–i, 8a–d, and 9–13, their BF2-β-ketoiminate complexes 5a–d, and BF2-β-diketonate complexes 6a–d were prepared as model substrates for photochemical...
Two pyrene derivatives, substituted at position 1 with isoxazole or NH-pyrazole, were synthesized in 85–87% yield starting from 1-acetylpyrene and via the cyclocondensation reaction of a β-enaminone intermediate with hydroxylamine or hydra...
Carbonic anhydrases (CAs) are a group of zinc-containing enzymes involved in many physiological processes through their role in the maintenance of the equilibrium between bicarbonate and CO2 levels. Human carbonic anhydrases (hCAs) are recognized as...
A total of 24 novel organocatalysts based on (S)-quininamine as a chiral tertiary amine and on enaminone or 1,2-benzenediamine as hydrogen bond donors were synthesized. The enaminone-type catalysts were prepared by the transamination of N,N-dimethyl...
Starting from acid chlorides, alkynes, tryptamines, and acryloyl chloride, 21 densely substituted tetrahydro-β-carbolines were prepared in a four-component, one-pot reaction. In this study, the aza-Michael addition step to generate intermediate...
Density functional theory (DFT) calculations at the M06-2X-D3/6-311++G(2df,2pd) level elucidate the mechanism and selectivity origins in the NHC-catalyzed divergent synthesis of spirocyclopentane oxindoles from isatin-derived enals and N-sulfonyl ket...