10220-22-1Relevant articles and documents
Palladium-catalysed Heck alkynylation of aryl bromides in an imidazolium ionic liquid: An unexpected subsequent alkyne hydrogenation reaction
Hierso, Jean-Cyrille,Picquet, Michel,Cattey, Hélène,Meunier, Philippe
, p. 3005 - 3008 (2006)
The copper-free palladium-catalysed alkynylation of aryl bromides with phenylacetylene in the imidazolium ionic liquid [BMIM][BF4], in the presence of triphenylphosphine ligand and pyrrolidine as a base, was found effective and significantly more chemoselective employing deactivated substrates. When activated aryl substrates were used, unexpected side reactions were observed, especially the subsequent hydrogenation of the alkyne function in some coupling products. In other cases, amine arylation reactions occurred, as illustrated by the formation of pyrrolidinyl-4-nitrobenzene, for which an X-ray diffraction structure is reported. Georg Thieme Verlag Stuttgart.
Room-Temperature Practical Copper-Catalyzed Amination of Aryl Iodides
Deldaele, Christopher,Evano, Gwilherm
, p. 1319 - 1328 (2016)
An efficient and highly practical procedure is reported for the Ullmann-Goldberg-type copper-catalyzed amination of aryl iodides. By using a combination of copper iodide and proline in the presence of an excess of an amine, a wide range of aryl iodides can be readily aminated at room temperature. The reaction proceeds well regardless of the electronic properties of the starting aryl iodide and the amination products can be obtained without the need for purification by column chromatography in most cases. Owing to its efficiency and the mildness of the reaction conditions, this amination could also be extended to the amination of complex aryl iodides at room temperature.
A palladium nanoparticle-catalyzed aryl-amine coupling reaction: High performance of aryl and pyridyl chlorides as the coupling partner
Nandi, Debkumar,Islam, Rafique Ul,Devi, Nishu,Siwal, Samarjeet,Mallick, Kaushik
, p. 812 - 816 (2018)
Carbon nitride (CN)-supported nanosized palladium particles, Pd-CN, have been found to be an active catalyst system for the amination of aryl and pyridyl chloride moieties in the presence of dialkyl amine under mild reaction conditions. The recyclability study of the reaction shows the stable performance of the catalyst without a significant loss of catalytic activity for a couple of cycles.
Cadmium(II)-catalyzed C-N cross-coupling of amines with aryl iodides
Rout, Laxmidhar,Saha, Prasenjit,Jammi, Suribabu,Punniyamurthy, Tharmalingam
, p. 395 - 398 (2008)
Cadmium diacetate dihydrate [Cd(OAc)2·2H2O] in combination with ethylene glycol catalyzes efficiently the C-N cross-coupling of amines with aryl iodides by a benzyne mechanism. Alkyl, aryl and heterocyclic amines are compatible with this system affording the aminated products in high to excellent yield.
Growth and characterization of a new organic single crystal: 1-(4-Nitrophenyl) pyrrolidine (4NPY)
Nirosha,Kalainathan,Aravindan
, p. 370 - 374 (2015)
A new 1-(4-Nitrophenyl) pyrrolidine single crystal has grown by slow evaporation solution growth technique. The grown crystal have characterized by single crystal X-ray analysis, and it shows that 1-(4-Nitrophenyl) pyrrolidine crystallizes in the orthorhombic space group Pbca, with cell parameters a = 10.3270 (5) A?, b = 9.9458 (6) A?, c = 18.6934 (12) A?, and Z = 8. Powder XRD pattern confirmed that grown crystal posses highly crystalline nature. The functional groups have identified by using FTIR spectral analysis. The absorbance and the luminescence spectra of the title compound have analyzed using UV-Visible and PL spectra. The thermo analytical properties of the crystal have studied using TG/DTA spectrum. The mechanical property of the grown crystal has determined using Vickers micro hardness measurement. The grown features of the crystal have analyzed using etching technique.
Integrating CuO?Fe2O3 Nanocomposites and Supramolecular Assemblies of Phenazine for Visible-Light Photoredox Catalysis
Kaur, Lovjot,Deol, Harnimarta,Kumar, Manoj,Bhalla, Vandana
, p. 892 - 898 (2020)
A photoredox catalytic ensemble consisting of CuO-Fe2O3 nanocomposites and oligomeric derivative of phenazine has been developed. The prepared system acts as an efficient photoredox catalyst for C?N bond formation reaction via SET mechanism under ‘green’ conditions (aerial environment, mixed aqueous media, recyclable), requiring less equivalents of base and amine substrate. The present study demonstrates the significant role of supramolecular assemblies as photooxidants and reductants upon irradiation and their important contribution towards the activation of the metallic centre through energy transfer and electron transfer pathways. The potential of oligomer 4: CuO-Fe2O3 has also been explored for C?C bond formation reactions via the Sonogashira protocol.
Optical fiber-based on-line UV/Vis spectroscopic monitoring of chemical reaction kinetics under high pressure in a capillary microreactor
Benito-Lopez, Fernando,Verboom, Willem,Kakuta, Masaya,Gardeniers,Egberink, Richard J. M.,Oosterbroek, Edwin R.,Van Den Berg, Albert,Reinhoudt, David N.
, p. 2857 - 2859 (2005)
With a miniaturized (3 μL volume) fiber-optics based system for on-line measurement by UV/Vis spectroscopy, the reaction rate constants (at different pressures) and the activation volumes (ΔV≠) were determinined for a nucleophilic aromatic substitution and an aza Diels-Alder reaction in a capillary microreactor. The Royal Society of Chemistry 2005.
Carbon-coated magnetic palladium: Applications in partial oxidation of alcohols and coupling reactions
Baig, R.B. Nasir,Nadagouda, Mallikarjuna N.,Varma, Rajender S.
, p. 4333 - 4338 (2014)
A carbon-coated magnetic Pd catalyst has been synthesized via in situ generation of nanoferrites and incorporation of carbon from renewable cellulose via calcination; the catalyst can be used for oxidation of alcohols, amination reaction and arylation of aryl halides (cross-coupling reaction). the Partner Organisations 2014.
Cobalt-catalyzed C-N bond-forming reaction between chloronitrobenzenes and secondary amines
Toma, Gabriel,Yamaguchi, Ryohei
, p. 6404 - 6408 (2010)
Cyclic secondary amines react with mono- or dichloronitrobenzene in the presence of a catalytic amount of cobalt(II) chloride. Phosphane ligands are beneficial for the reaction, although the bite-angle effect was not strong. The nitro-substituted tertiary amines formed are important as bioactive compounds and can also be intermediates for the synthesis of substituted anilines. This work represents the first cobalt-catalyzed approach to C-N bond-forming reactions involving aromatic chlorides and cyclic secondary amines. The reaction is ortho- and para-selective, with meta-substituted halides being unreactive in this procedure. The first cobalt-catalyzed C-N bond-forming reaction involving aromatic chlorides and cyclic secondary amines is described.The reaction is ortho- and para-selective; meta-substituted halides are unreactive. Copyright
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.
Practical direct synthesis of: N -aryl-substituted azacycles from N -alkyl protected arylamines using TiCl4and DBU
Kang, Soosung,Kim, Hee-Kwon,La, Minh Thanh,Tran, Van Hieu
, p. 5008 - 5016 (2020/07/30)
A novel transformation of N-alkyl protected arylamines and cyclic ethers into N-aryl substituted azacycles is described. Alkyl groups have been used for the protection of amines in organic syntheses. In this synthesis, N-alkyl protected arylamines were reacted with cyclic ethers in the presence of TiCl4 and DBU, crucial reagents affording five- and six-membered azacycles. In particular, utilization of the novel TiCl4/DBU-mediated reaction allows various N-alkyl protected arylamines such as N-methyl-, N-ethyl-, N-isopropyl, and N-tert-butyl arylamines to be readily converted into N-aryl substituted azacycles in high yields. This practical approach using various N-alkyl arylamines leads to the efficient preparation of azacycles.
Phenazine-Based Donor Acceptor Systems as Organic Photocatalysts for "metal-free" C-N/C-C Cross-Coupling
Deol, Harnimarta,Singh, Gurpreet,Kumar, Manoj,Bhalla, Vandana
, p. 11080 - 11093 (2020/10/12)
With an aim to achieve a balance between ground-state and excited-state reduction potential of donor acceptor systems for efficient C-N/C-C cross-coupling, a series of donor acceptor systems DA1-DA4 have been synthesized by varying the donor strength and connecting positions. With an increase in donor strength, systematic elevation in the ground-state reduction potential and decrease in the HOMO-LUMO gap was observed. Interestingly, all the derivatives DA1-DA4 could catalyze the C-N bond formation reaction between activated aryl halides and amines at low catalytic loading under metal-free conditions without the need of any external base upon irradiation with white LED. A balance was realized in the case of derivative DA2, which exhibits high efficiency in C-N couplings. Different control experiments support the validity of the energy as well as electron transfer pathways in the visible light-mediated C-N bond formation. This study further reveals the potential of derivative DA1 in "metal-free"Sonogashira coupling involving activated aryl halides which is attributed to its high excited-state reduction potential.
