56570-37-7

Upstream product

• 100-01-6 4-nitro-aniline 
• 123-54-6 acetylacetone 

Downstream Products

• 79257-46-8 diacetoxyacetylacetone-p-nitrophenyliminoboron 
• 100291-03-0 MoO₂Cl₂[CH₃C(O)CHC(NHC₆H₄NO₂)CH₃]2 

Relevant academic research and scientific papers

A simple protocol for the preparation of β-enamino ketones catalyzed by NbOPO4under solvent free conditions

A novel application of the highly stable niobium oxide phosphate (NbOPO4) as an efficient catalyst for the synthesis of β-enamino ketones under solvent-free conditions is described. This protocol, exhibits attractive yields, short reaction periods, lower loading of catalyst and high chemoselectivity.

Solvent-free synthesis of β-enamino ketones and esters catalysed by recyclable iron(III) triflate

A novel application of highly stable Fe(OTf)3 as an efficient catalyst for the synthesis of a variety of β-enamino ketones and esters under solvent-free conditions is described. Notably, this protocol of a "green synthesis", which produced β-enamino ketones and esters by the reaction of a variety of β-dicarbonyl compounds and primary amines, exhibits attractive properties including high yields, short reaction periods, lower loading of catalyst and chemo- and regio-selectivity. In addition, the catalyst was easily recovered from the reaction system and readily reused with minimal loss of activity.

Formic acid: A low-cost, mild, ecofriendly, and highly efficient catalyst for the rapid synthesis of β-enaminones

β-Enaminones have been synthesized by the condensation reaction of b-diketones with various anilines in the presence of a catalytic amount of formic acid, mild and highly efficient acid catalyst in methanol. These condensation reactions proceed smoothly in short reaction times with near-quantitative yields. Copyright

Zinc triflate catalysed synthesis of β-enamino ketones(esters) under solvent-free conditions

An efficient and mild procedure is described for the synthesis of a series of β-enamino ketones(esters) from 1,3-dicarbonyl compounds and aliphatic and aromatic amines using zinc triflate as the catalyst.

Approach to synthesis of Β-enamino ketones and pyrroles catalyzed by gallium(III) triflate under solvent-free conditions

Metal triflates have been used to catalyze synthesis of-enamino ketones or pyrroles from amines and 1,3-dicarbonyl or 1,4-dicarbonyl compounds under solvent-free conditions, respectively. Among different metal triflates screened, 0.5mol% Ga(OTf)3 efficiently promoted the reactions to give excellent yields. In addition, the catalyst could be recovered easily after the reactions and reused without evident loss in activity.

P2O5/SiO2 as a new, efficient, and reusable catalyst for preparation of β-enaminones under solvent-free conditions

P2O5/SiO2 (30% w/w) was applied as an efficient, heterogeneous, and reusable catalyst for the synthesis of β-enaminones. The reactions were rapidly completed at 80°C under solvent-free conditions and products were obtained in good to excellent yields. Copyright Taylor & Francis Group, LLC.

A general and efficient method for the preparation of β-enamino ketones and esters catalyzed by indium tribromide

A variety of β-enamino ketones and esters have been synthesized in high to exellent yields by reacting β-dicarbonyl compounds with amines in the presence of a catalytic amount of indium tribromide. The reaction proceeds smoothly at room temperature in a short reaction time under solvent-free conditions.

Ionic liquid promoted simple and efficient synthesis of β-enamino esters and β-enaminones from 1,3-dicarbonyl compounds - One-pot, three-component reaction for the synthesis of substituted pyridines

A facile enamination of 1,3-dicarbonyl compounds with amines has been developed that affords good to excellent yields of β-enamino esters and β-enaminones using Bronsted acidic ionic liquid 1-methylimidazolium trifluoroacetate ([Hmim]+Tfa-) at room temperature. This methodology has been extended for the synthesis of substituted pyridines in excellent yield by a one-pot, three-component reaction of 1,3-dicarbonyl compounds, ammonium acetate, and alkynone in the presence of [Hmim] +Tfa-.

Deuterium isotope effects on 13C chemical shifts of enaminones

Deuterium isotope effects on 13C chemical shifts have been studied in a series of substituted N-alkyl and N-phenyl keto-enamines. The intramolecularly hydrogen bonded Z-forms show the largest two-bond isotope effects, 2δC-1 (ND). Methyl-substitution at C-1 leads to a larger two-bond isotope effect in the N-phenyl-substituted derivatives. This effect is ascribed to steric compression. Space-filling substituents at the ortho-position of the N-phenyl ring lead to a decrease of the two-bond isotope effect. A correlation is found between 2δC-1(ND) and 3δC-2′(ND). The latter becomes negative in the sterically hindered cases. 3δC-2′(ND) may therefore be used as a gauge of the twist of the phenyl ring. o-Hydroxy substitution of the CO-phenyl rings enables intramolecular hydrogen bonding to the carbonyl group. This kind of hydrogen bond with two donors to one acceptor leads to smaller 2δC-2(ND) and 2δC-2″(OD) isotope effects equivalent to weaker hydrogen bonds for the Z-isomer. This is ascribed to competition for the acceptor. For the E-isomer 2δC(OD) is enhanced. The same feature is seen for N,N-dimethylamino enamines. This increase is ascribed to delocalization of the nitrogen lone-pair onto the carbonyl oxygen, thereby strengthening the hydrogen bond and thus leading to larger two-bond, 2δC(OD), isotope effects. Acta Chemica Scandinavica 1997.

NMR of enaminones part 3 ? - 1H, 13C and 17O NMR spectroscopic studies of acyclic and cyclic N-aryl enaminones: Substituent effects and intramolecular hydrogen bonding

17O, 13C and 1H NMR spectra for para-and meta-substituted 4-arylaminopent-3-en-2-ones (acyclic enaminones, 1 and 2) and 3-arylaminocyclohex-2-en-1-ones (cyclic enaminones, 3 and 4) are reported. The 17O, 13C and 1H shift values of these enaminones correlate well with σm0 and σp- constants in the correlations for meta and para derivatives, and with pKa values of the corresponding anilines. Dual substituent parameters analyses were also performed. Correlations of 17O and 13C chemical shifts of the carbonyl groups with those of the corresponding N-acylanilines indicate that the enaminone moiety as a whole has electronic properties similar to those of the RCONH group. The 17O shift values of the carbonyl O atoms of enaminones correlate well with their 1H and 13C data. Shieldings of 33-45 ppm for O atoms are observed for 1 and 2 compared with 3 and 4, respectively. This is attributed to intramolecular hydrogen bonding.