10389-51-2Relevant articles and documents
Pd-catalyzed conversion of aryl chlorides, triflates, and nonaflates to nitroaromatics
Fors, Brett P.,Buchwald, Stephen L.
, p. 12898 - 12899 (2009)
(Chemical Equation Presented) An efficient Pd catalyst for the transformation of aryl chlorides, triflates, and nonaflates to nitroaromatics has been developed. This reaction proceeds under weakly basic conditions and displays a broad scope and excellent
Exploring the influence of designer surfactant hydrophobicity in key C–C/C–N bond forming reactions
Reddy, Singarajanahalli Mundarinti Krishna,Kothandapani, Jagatheeswaran,Sengan, Megarajan,Veerappan, Anbazhagan,Selva Ganesan, Subramaniapillai
, p. 80 - 86 (2019)
Designer micellar medium was explored for the transformation of diverse anilines to the corresponding densely substituted biologically relevant skatole derivatives in an aqueous medium via 5-exo-trig cyclization reaction. The scope of the reaction was extended to intermolecular Csp2-Csp2 and Csp2-N bond forming reactions in water. Systematic investigations revealed that altering hydrophobicity of surfactant influences the yield of both C–C and C–N bond forming reactions in water.
Chitosan-Supported Ni particles: An Efficient Nanocatalyst for Direct Amination of Phenols
Hajipour, Abdol R.,Abolfathi, Parisa
, (2018)
A practical method for the direct amination of phenols using 2,4,6-trichloro-1,3,5-triazine (TCT) as an efficient promotor for the activation of phenols in the presence of an efficient and recyclable heterogeneous catalyst prepared by immobilization of nickel particles on triazole modified chitosan is described. This heterogeneous catalyst has demonstrated a promising activity for the conversion of phenolic compounds to their corresponding amine under mild conditions. Moreover, the obtained catalyst can be reused in five consecutive runs with consistent catalytic activity.
Controlled synthesis of water-dispersible faceted crystalline copper nanoparticles and their catalytic properties
Wang, Yanfei,Biradar, Ankush V.,Wang, Gang,Sharma, Krishna K.,Duncan, Cole T.,Rangan, Sylvie,Asefa, Tewodros
, p. 10735 - 10743 (2010)
We report a solution-phase synthetic route to copper nanoparticles with controllable size and shape. The synthesis of the nanoparticles is achieved by the reduction of copper(II) salt in aqueous solution with hydrazine under air atmosphere in the presence of poly(acrylic acid) (PAA) as capping agent. The results suggest that the pH plays a key role for the formation of pure copper nanoparticles, whereas the concentration of PAA is important for controlling the size and geometric shape of the nanoparticles. The average size of the copper nanoparticles can be varied from 30 to 80 nm, depending on the concentration of PAA. With a moderate amount of PAA, faceted crystalline copper nanoparticles are obtained. The as-synthesized copper nanoparticles appear red in color and are stable for weeks, as confirmed by UV/Vis and X-ray photoemission (XPS) spectroscopy. The faceted crystalline copper nanoparticles serve as an effective catalyst for N-arylation of heterocycles, such as the C-N coupling reaction between p-nitrobenzyl chloride and morpholine producing 4-(4-nitrophenyl) morpholine in an excellent yield under mild reaction conditions. Furthermore, the nanoparticles are proven to be versatile as they also effectively catalyze the three-component, one-pot Mannich reaction between p-substituted benzaldehyde, aniline, and acetophenone affording a 100% conversion of the limiting reactant (aniline).
An integrated flow and microwave approach to a broad spectrum protein kinase inhibitor
Russell, Cecilia,Lin, Andrew J. S.,Hains, Peter,Simone, Michela I.,Robinson, Phillip J.,Mccluskey, Adam
, p. 93433 - 93437 (2015)
The protein kinase inhibitor CTx-0152960 (6, 2-((5-chloro-2-((4-morpholinophenyl)amino)pyrimidin-4-yl)amino)-N-methylbenzamide), and the piperazinyl analogue, CTx-0294885 (7, 2-((5-chloro-2-((4-piperazin-1-ylphenyl)amino)pyrimidin-4-yl)amino)-N-methylbenzamide), were prepared using a hybrid flow and microwave approach. The use of flow chemistry approaches avoided the need for Boc-protection of piperidine in the key SNAr coupling with 1-fluoro-4-nitrobenzene. Microwave coupling of 4-morphilinoaniline 8 and 4-(piperazine-1-yl)aniline 9 with 2-(2,5-dichloropyrimidine-4-ylamino)-N-methylbenzamide 10, proved to be the most efficacious route to the target analogues 6 and 7. This hybrid methodology reduced the number of synthetic steps, gave enhanced overall yields and increased atom economy through step reduction and minimal requirement for chromatographic purification, relative to the original batch synthesis approach.
Synthesis and biological evaluation of some novel dithiocarbamate derivatives
Salik, Begüm Nurpelin,?zkay, Yusuf,Demir ?zkay, ümide,Karaca Gener, Hülya
, (2014)
18 novel dithiocarbamate derivatives were synthesized in order to investigate their inhibitory potency on acetylcholinesterase enzyme and antimicrobial activity. Structures of the synthesized compounds were elucidated by spectral data and elemental analyses. The synthesized compounds showed low enzyme inhibitory activity. However, they displayed good antimicrobial activity profile. Antibacterial activity of compounds 4a, 4e, and 4p (MIC = 25 g/mL) was equal to that of chloramphenicol against Klebsiella pneumoniae (ATCC 700603) and Escherichia coli (ATCC 35218). Most of the compounds exhibited notable antifungal activity against Candida albicans (ATCC 10231), Candida glabrata (ATCC 90030), Candida krusei (ATCC 6258), and Candida parapsilosis (ATCC 7330). Moreover, compound 4a, which carries piperidin-1-yl supstituent and dimethylthiocarbamoyl side chain as variable group, showed twofold better anticandidal effect against all Candida species than reference drug ketoconazole.
Recyclable bimetallic CuMoO4 nanoparticles for C-N cross-coupling reaction under mild conditions
Panigrahi, Reba,Panda, Subhalaxmi,Behera, Pradyota Kumar,Sahu, Santosh Kumar,Rout, Laxmidhar
, p. 19274 - 19278 (2019)
Herein we disclosed inexpensive copper(ii) bimetallic CuMoO4 nanoparticles for the C-N cross-coupling reaction of alkyl and aryl amines with haloarenes. The reaction proceeds under mild and ligand free conditions. The catalyst is recyclable and effective for a wide range of amines and haloarenes. Here, the efficiency of the Cu(ii) catalyst is increased by doping molybdenum metal. The bimetallic nanoparticles are anticipated to proceed via normal oxidative addition and reductive eliminations.
A coordination driven supramolecular Pd2L4self-assembly as heterogeneous catalyst for Buchwald-Hartwig amination reaction
Pradhan, Subhashis,Bhattacharyya, Arya,John, Rohith P.
, p. 1532 - 1536 (2016)
A Pd2L4type supramolecular coordination driven self assembly was constructed using a dipodal pyridyl terminal ligand L [L = N2,N6-dimethyl-N2,N6-bis((pyridin-4-yl)methyl)naphthalene-2,6-dicarboxamide] and palladium nitrate. The self-assembly was fully characterized by 1D and 2D NMR, ESI-MS, IR, TGA, HR-TEM and elemental analysis. The geometry optimization was performed using the Hartree-Fock method. The assembly acts as an efficient, reusable, heterogeneous catalyst for Buchwald-Hartwig amination reaction in toluene under phosphine free condition and aerobic medium.
Highly redox-stable and electrochromic aramids with morpholinyl-substituted triphenylamine units
Hsiao, Sheng-Huei,Hsiao, Ying-Hsiu,Kung, Yu-Ruei
, p. 1289 - 1298 (2016)
A novel morpholinyl-substituted, triphenylamine-based diamine monomer, namely 4,4′-diamino-4"-(4-morpholinyl)triphenylamine, was synthesized and polymerized with various aromatic dicarboxylic acids via the phosphorylation polyamidation reaction leading to a series of electroactive aromatic polyamides (aramids). All aramids were readily soluble in polar organic solvents and could be solution cast into tough and flexible films with high thermal stability. Cyclic voltammograms of the aramid films on the indium-tin oxide-coated glass substrate exhibited a pair of reversible oxidation waves with very low onset potentials of 0.36 - 0.41 V (vs. Ag/AgCl) in acetonitrile solution. The polymer films showed reversible electrochemical oxidation accompanied by strong color changes with high coloration efficiency, high contrast ratio, and rapid switching time. The optical transmittance change (Δ%T) at 650 nm between the neutral state and the fully oxidized state is up to 90%.
Deep Eutectic Solvent/Lipase: Two Environmentally Benign and Recyclable Media for Efficient Synthesis of N-Aryl Amines
Pant, Preeti Lalit,Shankarling, Ganapati Subray
, p. 1371 - 1378 (2017)
Abstract: Deep eutectic solvent (DES)/lipase catalyzed efficient synthesis of N-aryl amines from electron deficient aryl chlorides and amines at ambient temperature is reported. Its significant features include excellent yields of products, use of biodegradable, non-toxic and recyclable catalysts, thereby avoiding toxic metal catalyst/solvents making these protocols environmentally benign. Graphical Abstract: [Figure not available: see fulltext.].
Optimization of WZ4003 as NUAK inhibitors against human colorectal cancer
Yang, Huali,Wang, Xiaobing,Wang, Cheng,Yin, Fucheng,Qu, Lailiang,Shi, Cunjian,Zhao, Jinhua,Li, Shang,Ji, Limei,Peng, Wan,Luo, Heng,Cheng, Maosheng,Kong, Lingyi
, (2020/12/15)
NUAK, the member of AMPK (AMP-activated protein kinase) family of protein kinases, is phosphorylated and activated by the LKB1 (liver kinase B1) tumor suppressor protein kinase. Recent work has indicated that NUAK1 is a key component of the antioxidant stress response pathway, and the inhibition of NUAK1 will suppress the growth and survival of colorectal tumors. As a promising target for anticancer drugs, few inhibitors of NUAK were developed. With this goal in mind, based on NUAK inhibitor WZ4003, a series of derivatives has been synthesized and evaluated for anticancer activity. Compound 9q, a derivative of WZ4003 by removing a methoxy group, was found to be the most potential one with stronger inhibitory against NUAK1/2 enzyme activity, tumor cell proliferation and inducing apoptosis of tumor cells. By in vivo efficacy evaluations of colorectal SW480 xenografts, 9q suppresses tumor growth more effectively with an excellent safety profile in vivo and is therefore seen as a suitable candidate for further investigation.
Evidence for "cocktail"-type catalysis in Buchwald-Hartwig reaction. A mechanistic study
Ananikov, Valentine P.,Boiko, Daniil A.,Burykina, Julia V.,Madiyeva, Malena,Minyaev, Mikhail E.,Prima, Darya O.
, p. 7171 - 7188 (2021/11/17)
The mechanism of the C-N cross-coupling reaction, catalyzed by palladium complexes with N-heterocyclic carbene ligands (Pd/NHC), was evaluated in detail at the molecular and nanoscale levels. For the first time, the formation of a "cocktail"-type catalytic system was proven for the Buchwald-Hartwig reaction. The unique ability of the Pd/NHC system to generate several types of catalytic centers (Pd complexes, clusters and nanoparticles) and the involvement of complementary pathways (homogeneous and heterogeneous) were discovered to take place in a "one pot"manner directly in the reaction vessel. Access to various catalytic centers from a single and readily available Pd/NHC complex is the key to designing a universal catalytic system with adaptive tuning capability. This journal is