cas 2770-11-8, 2-(4-CHLOROPHENOXY)ANILINE | Articles data

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Pd-Co catalysts prepared from palladium-doped cobalt titanate precursors for chemoselective hydrogenation of halonitroarenes
Bimetallic Pd-Co catalysts supported on the mixed oxides CoTiO3-CoO-TiO2 (CTO) were synthesized via the thermal reduction of Pd-doped cobalt titanates PdxCo1-xTiO3 and evaluated for the chemoselective hydrogenation of halonitroarenes to haloarene-amines. The nominal Pd mass percentage of the Pd-Co/CTO systems was varied from 0.0 to 0.50. After the thermal reduction of PdxCo1-xTiO3 at 500 °C for 3 h, Pd was completely reduced and Co was partially reduced, producing a mixture of ionic Co, metallic Co, and TiO2-rutile species to give the supported bimetallic catalysts. The metallic cobalt content increased with the Pd content of the precursor. The catalytic activity toward 4-chloronitrobenzene increased with the Pd content; however, >0.1 mass% Pd decreased the chemoselectivity toward 4-chloroaniline due to the formation of the hydrodehalogenation product—aniline. The 0.1Pd-Co/CTO system was used as a model catalyst to produce haloarene-amine building blocks for linezolid, loxapine, lapatinib, and sorafenib with >98% conversion, 96% chemoselectivity, and no hydrohalogenation products. Finally, recycling tests of the 0.1Pd-Co/CTO catalyst showed loss of activity and selectivity during the third cycle due to catalyst deactivation. Regeneration treatments, every two catalytic cycles, allowed six operation cycles without loss of chemoselectivity and only a slight decrease in catalytic activity during the last cycle.
Bustamante, Tatiana M.,Dinamarca, Robinson,Torres, Cecilia C.,Pecchi, Gina,Campos, Cristian H.
(2019/12/24)

Promotional effect of palladium in Co-SiO2 core@shell nanocatalysts for selective liquid phase hydrogenation of chloronitroarenes
This study describes the synthesis of palladium-promoted Co@SiO2 catalyst developed by electrostatic immobilization of Pd ionic precursor onto Co3O4 nanoparticles core, coated with a mesoporous SiO2 shell. The oxidized Pd-Co3O4@SiO2 (xPdCo-ox) and partially reduced Pd-Co@SiO2 (xPdCo-red) nanocatalysts were used in the direct synthesis of chloro-arylamines from chloronitroarenes employing heterogeneous hydrogenation process. The effect of palladium content (xPdCo; x = 0.0, 0.5, 1.0 and 3.0 Pd wt%) in the Co3O4 core of the structures on catalytic performance for the hydrogenation of 4-chloronitrobenzene (CNB) to 4-chloroaniline (CAN) was systematically studied. It was found that the incorporation of palladium ionic precursor promotes both Co3O4 core nanoparticles flocculation and an increase in the mesoporous shell thickness in the Pd-promoted catalysts compared to the pristine Co-SiO2 core-shell structure. The TPR, XRD, XPS and magnetic measurements results indicated that the palladium addition promoted the reduction of Co3O4 core during the isothermal H2 treatment at 873 K rendering metallic Pd° and Co° species. The catalytic CNB hydrogenation experiments showed that the 0.5PdCo-red catalyst inhibited both the hydrodechlorination and intermediates accumulation reaching 99% yield in CAN compared to 1.0PdCo-red and 3.0PdCo-red catalysts which provided aniline as undesired product. Additionally, the 0.5PdCo-red catalyst was easily recycled with a moderate catalytic activity after five consecutive reaction cycles. Finally, the catalytic hydrogenation performance of the 0.5PdCo-red catalyst for different pharmaceutical substituted chloro-nitroarenes such as 1-(4-chlorophenoxy)-2-nitrobenzene, 2-chloro-1-((3-fluorobenzyl)oxy)-4-nitrobenzene and 2-chloro-5nitrobenzotrifluoride was also evaluated and revealed high activity (>99% at 3 h of reaction) and selectivity towards the desired chloro-arylmines production, highlighting the potential of this catalyst in these processes.
Bustamante, Tatiana M.,Campos, Cristian H.,Fraga, Marco A.,Fierro,Pecchi, Gina
p. 224 - 237
(2020/04/08)

Diphenyl ether derivatives occupy the expanded binding site of cyclohexanedione compounds at the colchicine site in tubulin by movement of the αT5 loop
Microtubule targeting agents represent a very active arena in the development of anticancer agents. In particular, compounds binding at the colchicine site in tubulin are being deeply studied, and the structural information recently available on this binding site allows structure-directed design of new ligands. Structural comparison of our recently reported high resolution X-Ray structure of the cyclohexanedione derivative TUB075 bound to tubulin and the tubulin-DAMA-colchicine complex has revealed a conformational change in the αT5 loop. By a grid-based computational analysis of the tubulin-DAMA-colchicine binding site, we have identified a new favourable binding area in the colchicine-site that was unexplored by our lead TUB075. Thus, based on a structure-guided design, new cyclohexanedione derivatives have been synthesized and tested for tubulin binding and in cellular assays. As a result, we have identified diphenyl ether derivatives with IC50 values around 10–40 nM against three different tumor cell lines and affinity constants for tubulin similar to that of colchicine around 107 M?1. As expected, they halted the cell cycle progression at G2/M phase at concentrations as low as 0.08 μM.
Bueno, Oskia,Gargantilla, Marta,Estévez-Gallego, Juan,Martins, Solange,Díaz, J. Fernando,Camarasa, María-José,Liekens, Sandra,Pérez-Pérez, María-Jesús,Priego, Eva-María
p. 195 - 208
(2019/03/28)

Synthesis of medium-sized (6-7-6) ring compounds by iron-catalyzed dehydrogenative C-H activation/annulation
In this report, we have described a FeCl3-catalyzed process involving intramolecular annulation of o-phenoxy diarylacetylenes via hydroarylation to afford a series of biologically potent fused seven-membered (6-7-6) ring compounds under mild reaction conditions. This reaction was believed to proceed through Friedel-Crafts type sequential carbometallation followed by protonation to produce phenyldibenz[b,f]oxepines. This method was also extended to synthesize seven-membered rings that are fused with coumarins.
Panda, Niranjan,Mattan, Irshad,Ojha, Subhadra,Purohit, Chandra Shekhar
p. 7861 - 7870
(2018/11/21)

Pyrazinamide compounds and preparing method and application thereof and bactericide
The invention relates to the field of pesticide bactericides, and discloses a pyrazinamide compound and a preparing method and application thereof and a bactericide. The pyrazinamide compound has thestructure shown in the formula (I) or the formula (II) or the formula (III). According to the pyrazinamide compound and the preparing method and application thereof and the bactericide, by introducingpyrazine ring fragments and and diphenyl ether fragments with the wide biological activity in NNF-0721, and the pyrazinamide compound with the brand-new structure is designed; the pyrazinamide compound can serve as a brand-new succinodehydrogenase inhibitor or a bactericide. The formula is defined in the description.
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Paragraph 0141; 0142; 0144; 0146

(2019/01/14)

Access to Chiral Seven-Member Cyclic Amines via Rh-Catalyzed Asymmetric Hydrogenation
A highly efficient asymmetric hydrogenation of azepine/oxazepine-type seven-member cyclic imine hydrochlorides was successfully developed using Rh/bisphosphine-thiourea ligand ZhaoPhos, affording various chiral seven-member cyclic amines with full conversions, high yields, and excellent enantioselectivities (up to 96% yield, >99% ee). Additionally, this asymmetric hydrogenation can proceed well on gram scale with excellent ee value. Moreover, control experimental results displayed that the anion-bonding interaction between the chloride ion of the substrate and thiourea motif of the ZhaoPhos played an important role to obtain excellent enantioselectivity.
Li, Pan,Huang, Yi,Hu, Xinquan,Dong, Xiu-Qin,Zhang, Xumu
p. 3855 - 3858
(2017/07/26)

Design, synthesis and antifungal activity of novel furancarboxamide derivatives
Twenty-seven novel furancarboxamide derivatives with a diphenyl ether moiety were synthesized and evaluated for their antifungal activity against Rhizoctonia solani, Botrytis cirerea, Valsa Mali and Sphaceloma ampelimum. Antifungal bioassay results indicated that most compounds had good or excellent fungicidal activities for R. solani and S. ampelimum at 20 mg L-1. Among synthesized compounds, compound 18e showed a greater inhibitory effect against S. ampelimum, with half maximal effective concentration (EC50) values of 0.020 mg L-1. This strong activity rivals currently used commercial fungicides, such as Boscalid and Carbendazim, and has great potential as a lead compound for future development of novel fungicides.
Wen, Fang,Jin, Hong,Tao, Ke,Hou, Taiping
p. 244 - 251
(2016/05/24)

Additivity of substituent effects in aromatic stacking interactions
The goal of this study was to experimentally test the additivity of the electrostatic substituent effects (SEs) for the aromatic stacking interaction. The additivity of the SEs was assessed using a small molecule model system that could adopt an offset face-to-face aromatic stacking geometry. The intramolecular interactions of these molecular torsional balances were quantitatively measured via the changes in a folded/unfolded conformational equilibrium. Five different types of substituents were examined (CH3, OCH3, Cl, CN, and NO2) that ranged from electron-donating to electron-withdrawing. The strength of the intramolecular stacking interactions was measured for 21 substituted aromatic stacking balances and 21 control balances in chloroform solution. The observed stability trends were consistent with additive SEs. Specifically, additive SE models could predict SEs with an accuracy from ±0.01 to ±0.02 kcal/mol. The additive SEs were consistent with Wheeler and Houk's direct SE model. However, the indirect or polarization SE model cannot be ruled out as it shows similar levels of additivity for two to three substituent systems, which were the number of substituents in our model system. SE additivity also has practical utility as the SEs can be accurately predicted. This should aid in the rational design and optimization of systems that utilize aromatic stacking interactions.
Hwang, Jungwun,Li, Ping,Carroll, William R.,Smith, Mark D.,Pellechia, Perry J.,Shimizu, Ken D.
p. 14060 - 14067
(2015/01/08)

COMPOUND
There is provided a compound having Formula (I) wherein each of R1, R2, R4, R5, R6 and R7 are independently selected from (a) H, (b) R17, -OC(R17)3, -OCH(R17)2, -(OCH2R)17, -C(R17)3, -CH(R17)2, or -CH2R17 wherein R17 is a halogen; (c) -CN; (d) optionally substituted alkyl, (e) optionally substituted heteroalkyl; (f) optionally substituted aryl; (g) optionally substituted heteroaryl; (h) optionally substituted arylalkyl; (i) optionally substituted heteroarylalkyl; (j) hydroxy; (k) alkoxy; (l) aryloxy; (m) -SO2-alkyl; and (n) -N(R11)C(O)R13; wherein the optional substituents of (d) (e) (f) (h) and (i) are selected from the group consisting of: C1-6 alkyl, halo, cyano, nitro, haloalkyl, hydroxy, alkoxy, carboxy, carboxyalkyl, carboxamide, mercapto, amino, alkylamino, dialkylamino, sulfonyl, sulfonamido, aryl and heteroaryl ; each of rings A and B are selected from five or six membered carbon rings optionally containing one or more hetero atoms selected from N, S, and O and optionally having fused thereto a further ring; X is an optional group selected from O, S, S=O, S(=O)2, C=O, S(=O)2NR8, C=ONR9, NR10, wherein R8, R9 and R10 are independently selected from H and hydrocarbyl, wherein n and p are independently selected from O and 1 ; Y is (R11)1-3 wherein each R11 is independently selected from NR12, CR13R14, S(=O)2 and C=O, wherein R12, R13 and R14 are independently selected from H and hydrocarbyl; Z is selected from (i) six or seven membered ring containing carbon and at least one nitrogen, which may be optionally substituted wherein the substituents may together form further ring fused thereto; and (ii) a -R15-NR16- group wherein R15 is an optionally substituted C1-6 alkyl chain and R16 is selected from H and hydrocarbyl; and R3 is selected from Formula (A).
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Page/Page column 119

(2008/06/13)

Electrocarboxylation of chlorinated aromatic compounds
Chorinated benzenes (1, 4), biphenyls (6, 9), dibenzofurans (10, 15, 17, 18), 2-chlorodibenzo[1,4]dioxine (24) and 1-chloronaphthalene (26) as well as dibenzofuran (12) and naphthalene (27) themselves were transformed into carboxylic acids by galvanostatic electroreduction in the presence of carbon dioxide ("electrocarboxylation"). Dry DMF was used as solvent, zinc or stainless steel as cathode and magnesium as a sacrificial anode in an undivided cell. Hydrogenation of aromatic rings was not observed. However, reductive addition of two molecules of carbon dioxide to form dihydrodicarboxylic acids, e.g. 22 and 29, occurs in the dibenzofuran and naphthalene series.
Golinske, Dirk,Voss, Juergen,Adiwidjaja, Gunadi
p. 862 - 880
(2007/10/03)