- Selective reduction of nitro group in aryl halides catalyzed by silver nanoparticles modified with β-CD
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In this paper, we first report the selective reduction of nitro group in aryl halides catalyzed by silver nanoparticles modified with β-CD. Taking advantage of hydrophobic lumen and donor-acceptor behavior of β-CD, the halogenated alkyl groups on the aromatic ring can be enveloped in the inner cavity that thereby inhibits the reduction of the halogen. For validating the mechanism proposed by us, different silver nanoparticles were applied in parallel experiments. In our experiments, UV-vis spectra and NMR spectra were used to characterize the selectivity. This strategy represents an outstanding improvement on the synthesis of halogenated aromatic amines in comparison with the traditional route, and greatly expands the application of silver nanoparticles in catalytic field.
- Ding, Xu,Zhu, Geng,Guan, Jian-Ning,Han, Guo-Zhi
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- Synthesis and Characterization of Hydroxy Substituted Pyridinium Type of Ionic Liquids via Conventional/ Silica Supported Approaches and Their Applications
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Synthesis of 2-hydroxy pyridinium type of ionic liquids is obtained via conventional as well as silica-supported approaches. We found that solid-supported reaction under muffle furnace condition has reduced the reaction nearly 20 times shorter than the co
- Manikandan, Chitrarasu,Ganesan, Kilivelu
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- Ultra-low-loading palladium nanoparticles stabilized on nanocrystalline Polyaniline (Pd@PANI): A efficient, green, and recyclable catalyst for the reduction of nitroarenes
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Ultra-low-loading Pd@PANI nanocomposites (0.048 w.t% Pd) were synthesized via a method that combined interfacial polymerization and in situ composite with camphor sulfonic acid ((+)-CSA) as a dopant. Transmission electron microscopy (TEM), X-ray diffraction (XRD), Fourier transform infrared (FTIR) spectra, and X-ray photoelectron spectroscopy (XPS) were performed to characterize the structures. It can be used as an efficient catalyst for the reduction of nitroarenes in aqueous solution by using a smaller amount of NaBH4 (2.5 equiv.) at room temperature with high activity (TON?=?3.4?×?103), good stability (cycled eight times), as well as wide applicability (27 substrates). The catalyst also showed a marvelous activity in the gram-level reaction (yield?=?92%). UV–Visible spectrophotometry was used to investigate the reaction kinetics for the reduction of 4-nitrophenol to 4-aminophenol, and the results reconfirmed the excellent performance of the catalyst. The unique properties and superior performance of the prepared ultra-low-loading Pd@PANI nanocomposites lead it be an attractive alternative catalyst for conventional organic catalytic applications.
- Wang, Gang,Yuan, Shuo,Wu, Zhiqiang,Liu, Wanyi,Zhan, Haijuan,Liang, Yanping,Chen, Xiaoyan,Ma, Baojun,Bi, Shuxian
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- Rapid and convenient conversion of nitroarenes to anilines under microwave conditions using nonprecious metals in mildly acidic medium
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Nitroarenes are reduced to the corresponding aniline derivatives using iron or zinc under mild conditions under microwave heating conditions. Mild acidity is provided by ammonium chloride in an aqueous methanol medium. The conditions are tolerant to other functional groups, with the exception of bromoalkyl derivatives, which yield complex reaction mixtures; otherwise, yields are generally quite high (80–99%).
- Keenan, Corey S.,Murphree, S. Shaun
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supporting information
p. 1085 - 1089
(2017/05/25)
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- Synthesis and Biological Evaluation of 1,2,3-triazole tethered Pyrazoline and Chalcone Derivatives
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A series of pyrazoline derivatives and corresponding chalcone intermediates with substituents same as combretastatin-A4(CA-4) conjugated with triazole nucleus has been synthesized and evaluated for their anticancer potential. Sulphorhodamine B(SRB) assay indicated compound 12c to be the most active compound from the series with GI50 value of 6.7 μm against the human liver carcinoma cell line HepG2. Interestingly, the intermediate 11c exhibited more promising cytotoxicity demonstrating GI50 value of 1.3 μm against the prostate cancer cell line DU145. Compounds 11c and 12c caused accumulation of cells in G2/M phase and inhibited tubulin polymerization. Furthermore, these compounds reduce the mitochondrial membrane potential and activate caspases 3 and 9, thereby indicating their ability to trigger apoptosis.
- Hussaini, Syed Mohammed Ali,Yedla, Poornachandra,Babu, Korrapati Suresh,Shaik, Thokhir B.,Chityal, Ganesh Kumar,Kamal, Ahmed
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- Highly efficient and chemoselective transfer hydrogenation of nitroarenes at room temperature over magnetically separable Fe-Ni bimetallic nanoparticles
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A highly chemoselective catalytic transfer hydrogenation (CTH) of nitroarenes to corresponding amino derivatives is achieved with Fe-Ni bimetallic nanoparticles (Fe-Ni NP's) as the catalyst and NaBH4 at room temperature. Their catalytic efficiency is ascribed to the presence of Ni sites on the bimetallic surface that not only hinder the surface corrosion of the iron sites but also facilitate efficient electron flow from the catalyst surface to the adsorbed nitro compounds. This facet is corroborated with reusability studies as well as surface characterization of the catalyst before and after its repetitive usage. Thus, these nanoparticles efficiently catalyze the reduction of functionalized nitroarenes to corresponding amines without use of corrosive agents like base or other additives under ambient conditions and are easily separated by a laboratory magnet in an eco-friendly manner.
- Petkar, Dhananjay R.,Kadu, Brijesh S.,Chikate, Rajeev C.
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p. 8004 - 8010
(2014/02/14)
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- Synthesis and evaluation of technical properties of novel cationic mono-s-chloro triazinyl (MCT) reactive dyes on cotton
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Two novel cationic mono-s-chloro triazinyl (MCT) reactive dyes together with their analogues were synthesized via reacting an N,N-dimethyl dodecylamine with p-nitrobenzyl bromide. The resultant was reduced using stannous chloride and hydrochloric acid to produce the primary amine. The quaternary ammonium salt containing primary amine was then diazotized and coupled to H-acid/J-acid reacted with cyanuric chloride and sulfanilic acid. The analogue dyes were prepared via the same route without quaternary ammonium salt making stage. The dyes were characterized using FTIR, 1H NMR, UV-Vis spectroscopy and elemental analysis. The substantivity, exhaustion and fixation of the dyes were investigated on cotton fabric. It was found that these functional dyes could be effectively introduced to cotton for achieving simultaneous coloration and functional finishing effects. All the dyed fabrics exhibited softening efficacy. The washing and light fastness of the dyed samples were further studied.
- Javadi, Marzieh S.,Mokhtari, Javad
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experimental part
p. 793 - 801
(2012/08/28)
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- Conversion of systemically-distributed triazole-based stearoyl-CoA desaturase (SCD) uHTS hits into liver-targeted SCD inhibitors
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It has been demonstrated that once-a-day dosing of systemically-distributed SCD inhibitors leads to adverse events in eye and skin. Herein, we describe our efforts to convert a novel class of systemically-distributed potent triazole-based uHTS hits into liver-targeted SCD inhibitors as a means to circumvent chronic toxicity.
- Leclerc, Jean-Philippe,Falgueyret, Jean-Pierre,Girardin, Mélina,Guay, Jocelyne,Guiral, Sébastien,Huang, Zheng,Li, Chun Sing,Oballa, Renata,Ramtohul, Yeeman K.,Skorey, Kathryn,Tawa, Paul,Wang, Hao,Zhang, Lei
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scheme or table
p. 6505 - 6509
(2011/12/04)
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- Efficient reduction of nitroarenes to the corresponding anilines with sulfur in basic media under solvent-free conditions
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Aromatic nitro compounds can be conveniently reduced to the corresponding primary amines in the presence of S8 under solvent-free conditions in excellent yields. Alumina supported NaOH catalyses this transformation. Chemoselectivity was observed in the reduction of the nitro group in the presence of phenol, carboxylic acid, aldehyde, and benzyl halide groups.
- Niknam, Khodabakhsh,Kiasat, Ali Reza,Kazemi, Foad,Hossieni, Abolghasem
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p. 1385 - 1389
(2007/10/03)
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- Anilide derivative, production and use thereof
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This invention is to provide a compound of the formula: wherein R1is an optionally substituted 5- to 6-membered ring; the ring A is an optionally substituted 6- to 7-membered ring; the ring B is an optionally substituted benzene ring; n is an integer of 1 or 2; Z is a chemical bond or a divalent group; R2is (1) an optionally substituted amino group in which a nitrogen atom may form a quaternary ammonium, (2) an optionally substituted nitrogen-containing heterocyclic ring group which may contain a sulfur atom or an oxygen atom as ring constituting atoms and wherein a nitrogen atom may form a quaternary ammonium, (3) a group binding through a sulfur atom or (4) a group of the formula: ?wherein k is 0 or 1, and when k is 0, a phosphorus atom may form a phosphonium; and R5and R6are independently an optionally substituted hydrocarbon group, an optionally substituted hydroxy group or an optionally substituted amino group, and R5and R6may bind to each other to form a cyclic group together with the adjacent phosphorus atom, or a salt thereof , which is useful for antagonizing CCR5 and also for the prevention and treatment of infectious disease of HIV.
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- Multi-electron Reduction of Nitrobenzene Derivatives by an Acid-stable NADH Analogue via Acid-Catalysed Electron Transfer Radical-chain Reactions
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Acid catalysed multi-electron reduction of nitrobenzene derivatives by an acid-stable NADH analogue, 10-methyl-9,10-dihydroacridine, occurs efficiently under mild conditions in the presence of perchloric acid in acetonitrile.Observation of CIDNP spectra as well as detailed kinetic studies on the acid catalysed reduction of nitrobenzene derivatives by AcrH2 and on the acid catalysed electron transfer from the excited state of 2+ to nitrobenzene derivatives has revealed that the multi-electron reduction of nitrobenzene derivatives by AcrH2 proceeds via acid catalysed electron transfer radical-chain reactions in which hydrogen from AcrH2 to radicals produced by the acid catalysed one-electron reduction of nitrobenzene derivatives is the rate determining propagation step.
- Fukuzumi, Shunichi,Chiba, Makoto
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p. 1393 - 1398
(2007/10/02)
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- Acid-catalysed Multi-electron Reduction of Nitrobenzene Derivatives by a Dihydronicotinamide Adenine Dinucleotide (NADH) Model Compound, 9,10-Dihydro-10-methylacridine
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Acid-catalysed multi-electron reduction of nitrobenzene derivatives by a dihydronicotinamide adenine dinucleotide (NADH) model compound proceeds efficiently under mild conditions in the presence of perchloric acid in acetonitrile.
- Fukuzumi, Shunichi,Chiba, Makoto,Tanaka, Toshio
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p. 941 - 943
(2007/10/02)
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