116546-10-2Relevant academic research and scientific papers
Lanthanum(III)-Catalyzed Three-Component Reaction of Coumarin-3-carboxylates for the Synthesis of Indolylmalonamides and Analysis of Their Photophysical Properties
Jennings, Julia J.,Bhatt, Chinmay P.,Franz, Annaliese K.
, p. 6211 - 6222 (2016)
New methodology has been developed for the Lewis acid catalyzed synthesis of malonamides. First, the scandium(III)-catalyzed addition of diverse nucleophiles (e.g., indoles, N,N-dimethyl-m-anisidine, 2-ethylpyrrole, and 2-methylallylsilane) to coumarin-3-carboxylates has been developed to afford chromanone-3-carboxylates in high yields as a single diastereomer. Upon investigating a subsequent lanthanum(III)-catalyzed amidation reaction, a new multicomponent reaction was designed by bringing together coumarin-3-carboxylates with indoles and amines to afford indolylmalonamides, which were identified to exhibit fluorescent properties. The photophysical properties for selected compounds have been analyzed, including quantum yield, molar absorptivity, and Stokes shift. Synthetic studies of several reaction byproducts involved in the network of reaction equilibria for the three-component reaction provide mechanistic insight for the development of this methodology.
AIPE-active platinum(ii) complexes with tunable photophysical properties and their application in constructing thermosensitive probes used for intracellular temperature imaging
Lin, Shengheng,Pan, Honghao,Li, Lin,Liao, Rui,Yu, Shengzhen,Zhao, Qiang,Sun, Huibin,Huang, Wei
, p. 7893 - 7899 (2019)
Aggregation-induced phosphorescent emission (AIPE) luminogens based on phosphorescent transition metal complexes have many application advantages in bioimaging compared with fluorescent organic dyes because of their long excitation lifetime and reduced ph
The substituent effects on the 13C chemical shifts of the azomethine carbon atom of N-(substituted phenyl)salicylaldimines
Drmanic, Sasa Z.,Marinkovic, Aleksandar D.,Nikolic, Jasmina B.,Jovanovic, Bratislav Z.
, p. 993 - 1001 (2012)
Hammett correlations between the 13C-NMR chemical shifts of the azomethine carbon atom and the corresponding substituent constants were established for thirteen Schiff bases. The successful correlation of the chemical shifts with the electrophilic substituent constants σ+ indicate a significant resonance interaction of the substituents on the aniline ring with the azomethine carbon atom in the examined series of imines. The demand for electrons in the investigated compounds was compared to that of the N-benzylideneanilines and N-(substituted phenyl)pyridinealdimines. The manner of transmission of the substituent effects is discussed and they were separated into resonance and inductive effects. The inductive effects prevail over the resonance effects.
The effect of solvent on electronic absorption bands of some Benzylideneanilines
Panigrahi, Sagarika,Misra, Pramila K.
, p. 53 - 61 (2016)
In the present investigation the effects of solvents of varied polarities on the UV–visible spectral bands of some substituted benzylideneanilines and their o/p-hydroxy derivatives were explored. The analyses of the electronic absorption bands indicated t
Influence of substituents on the structure of Schiff bases Cu(II) complexes
Xiao, Yan,Cao, Chenzhong
, (2020)
The relationship between molecular conformation and substituent effects of salicylaldehyde Schiff-base Cu(II) complexes was explored. For this study, eight samples of the complexes Cu(Sal-X)2 (X = OMe, Me, H, F, Cl, Br, CF3 and CN) w
A novel water-dispersible and magnetically recyclable nickel nanoparticles for the one-pot reduction-Schiff base condensation of nitroarenes in pure water
Ghamari Kargar, Pouya,Ravanjamjah, Asiye,Bagherzade, Ghodsieh
, p. 1916 - 1933 (2021/07/10)
In this work, a heterogeneous nanocatalyst called Ni-Fe3O4@Pectin~PPA ~ Piconal was first synthesized, which was investigated as a bifunctional catalyst containing nickel functional groups. On the other hand, this Ni-Fe3O4@Pectin~PPA ~ Piconal catalyst in aqueous solvents shows a very effective performance at ambient temperature for the nitroarene reduction reaction with sodium borohydride, for which NaBH4 is considered as a reducing agent. This is a novelty magnetic catalyst that was approved by various methods, including Fourier-transform infrared spectroscopy (FT-IR), X-ray powder diffraction (XRD), Dynamic light scattering (DLS), Transmission electron microscopy (TEM), vibrating sample magnetometer (VSM), Inductively coupled plasma (ICP), Energy-dispersive X-ray spectroscopy (EDX), and Field emission scanning electron microscopy (FESEM) analyses. From the satisfactory results obtained from the reduction of nitrogen, this catalytic system is used for a one-pot protocol containing a reduction-Schiff base concentration of diverse nitroarenes. It was corroborated with the heterogeneous catalytic experiments on the one-pot tandem synthesis of imines from nitroarenes and aldehydes. Finally, the novel Ni-Fe3O4@Pectin~PPA ~ Piconal catalyst could function as a more economically desirable and environmentally amicable in the catalysis field. The favorable products are acquired in good to high performance in the attendance of Ni-Fe3O4@Pectin~PPA ~ Piconal as a bifunctional catalyst. This catalyst can be recycled up to six steps without losing a sharp drop.
Simple synthesis of the novel Cu-MOF catalysts for the selective alcohol oxidation and the oxidative cross-coupling of amines and alcohols
Ghamari Kargar, Pouya,Aryanejad, Sima,Bagherzade, Ghodsieh
, (2020/09/11)
A novel porous metal–organic framework {Cu2(bbda)0.5(Hbbda)1.5(OAc)1.5.8H2O} (UoB-5) was synthesized under ultrasound irradiation by employing a new Schiff base ligand H2bbda (4,4'(1,4-phenylene bis (azanylylidene)) bis (methanylylidene))dibenzoic acid) and was fully characterized. The microporous nature of UoB-5 was confirmed by gas-sorption measurements. This framework acted as a highly effective heterogeneous catalyst for the alcohol oxidation reaction with tert-butyl hydroperoxide (t-BuOOH) as an oxidant. The presence of coordinatively unsaturated metal sites in UoB-5 could be the reason for high performance in this reaction. Furthermore, using the long linker with the free -NC group and uncoordinated -N atom on the wall of the pores created UoB-5 an excellent candidate for the catalytic activities without activation of the framework. It was confirmed with the heterogeneous catalytic experiments on the one-pot tandem synthesis of imines from benzyl alcohols and anilines. Eventually, the new Cu-MOF (UoB-5) could be an alternative catalyst as a more economically favorable and environmentally friendly in the catalysis field.
Design, synthesis, and biological activity of Schiff bases bearing salicyl and 7-hydroxycoumarinyl moieties
Hejchman, El?bieta,Kruszewska, Hanna,Maciejewska, Dorota,Sowirka-Taciak, Barbara,Tomczyk, Magdalena,Sztokfisz-Ignasiak, Alicja,Jankowski, Jan,M?ynarczuk-Bia?y, Izabela
, p. 255 - 266 (2019/01/16)
Abstract: 18 (11 novel) Schiff bases, derivatives of salicylaldehyde, 2-hydroxyacetophenone, and 6-acetyl-, 8-acetyl-, and 8-formyl-7-hydroxy-4-methylcoumarin were synthesized and characterized by their spectral studies. 6-Acetyl-7-hydroxy-4-methylcoumarin was prepared by novel method under microwave assistance. These Schiff bases were evaluated for antibacterial activities against 12 bacterial and six fungi strains in vitro. N-(3,5-Dichloro-2-hydroxybenzylidene)-4-aminobenzenesulfonic acid sodium salt proved to be the most active against Staphylococcus aureus and MRSA strains (MIC 0.0194?μmol/cm3). The substitution pattern, two chlorine atoms in the salicylidene ring and the SO3Na group, is probably the most beneficial for the activity against Gram-(+) bacteria strains. All Schiff bases were evaluated for cancer efficacy against CFPAC-1 and HeLa cell cultures originating from human pancreas cancer or human cervical cancer. Schiff bases derived from salicylaldehyde are highly effective in pancreas and cervical cancer cells; however, they demonstrate also substantial toxicity towards NIH3T3 cells. Derivatives of coumarin contain three highly selective compounds: 7-hydroxy-8-[(4-methoxyphenylimino)methyl]-4-methyl-2H-chromen-2-one, N-[(7-hydroxy-4-methyl-2-oxo-2H-chromen-8-yl)methylene]-4-aminobenzenesulfonic acid sodium salt, and 7-hydroxy-8-[1-(4-hydroxyphenylimino)ethyl]-4-methyl-2H-chromen-2-one suggesting more promising potential of the second group of substances.
Improving C=N bond reductions with (Cyclopentadienone)iron complexes: Scope and limitations
Cettolin, Mattia,Bai, Xishan,Lübken, Dennis,Gatti, Marco,Facchini, Sofia Vailati,Piarulli, Umberto,Pignataro, Luca,Gennari, Cesare
supporting information, p. 647 - 654 (2018/10/24)
Herein, we broaden the application scope of (cyclo-pentadienone)iron complexes 1 in C=N bond reduction. The catalytic scope of pre-catalyst 1b, which is more active than the “Kn?lker complex” (1a) and other members of its family, has been expanded to the catalytic transfer hydrogenation (CTH) of a wider range of aldimines and ketimines, either pre-isolated or generated in situ. The kinetics of 1b-promoted CTH of ketimine S1 were assessed, showing a pseudo-first order profile, with TOF = 6.07 h–1 at 50 % conversion. Moreover, the chiral complex 1c and its analog 1d were employed in the enantioselective reduction of ketimines and reductive amination of ketones, giving fair to good yields and moderate enantioselectivity.
Effect of substituents on the UV spectra of supermolecular system: Silver nanoparticles with bi-aryl Schiff bases containing hydroxyl
Cao, Chao-Tun,Cheng, Shimao,Zhang, Jingyuan,Cao, Chenzhong
, (2018/11/25)
Effect of substituents on the ultraviolet (UV) spectra of supermolecular system involving silver nanoparticles (AgNPs) and Schiff bases was investigated. AgNPs and 49 samples of model compounds (MC), bi-aryl Schiff bases containing hydroxyl (XBAY, involving 4-OHArCH?NArY, 2-OHArCH?NArY, XArCH?NAr-4′-OH, and XArCH?NAr-2′-OH), were synthesized. The size of AgNPs was characterized by transmission electron microscopy (TEM), and the UV absorption spectra of AgNPs, XBAYs, and MC-AgNPs mixed solutions were measured, respectively. The results show that (1) the size of AgNPs is larger in MC-AgNPs solutions than that in AgNPs solution due to the distribution of MC molecules on the surface of AgNPs; (2) the UV absorption wavelength of XBAYs changes in the action of AgNPs and their wavelength shift exists limitation between XBAY and MC-AgNPs solutions; and (3) the wavelength shift limit of MC-AgNPs (λWSL) is influenced by the substituents X and Y and the position of hydroxyl OH. The wavenumber ΔνWSL of λWSL can be quantified by employing the excited-state substituent constant σexCC and Hammett constant σ of substituents X and Y. Comparing with the 4-OH, the 4′-OH makes the ΔνWSL a red shift, whereas the 2′-OH, comparing with the 2-OH, makes the ΔνWSL a blue shift.
