- Preparation and characterization of Cu based on 5,5'-bistetrazole as a recyclable metal-organic framework and application in synthesis of diaryl ether by the Ullmann coupling reaction
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Cu based on 5,5′-bistetrazole ([Cu2BT · 2H2O] n) as a recyclable metal-organic framework (MOF) heterogeneous catalyst was characterized by FT-IR, 13C NMR, XRD, SEM, EDX, BET, BJH, and ICP-AES analysis. The catalytic activity of the catalyst was probed through the Ullmann reaction for synthesis of diaryl ether derivatives from two component reactions of aromatic arylhalides and phenol derivatives in DMSO. Simple procedure, high yields, short reaction time, and environmentally benign methods are advantages of this protocol. The catalyst was readily separated by simple filtration and reusable without significant loss of its catalytic efficiency.
- Noorpoor, Zeinab,Tavangar, Saeed
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p. 1651 - 1662
(2021/05/10)
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- Pd based on 2-Aminopyrimidine and 1H-benzo[d]imidazol-2-amine functionalizedFe3O4 nanoparticles as novel recyclable magnetic nanocatalysts for Ullmann coupling reaction
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In this study, Pd based on 2-Aminopyrimidine and 1H-benzo[d]imidazol-2-amine functionalized Fe3O4 magnetic nanoparticles [(Pd-APM-PSi-Fe3O4) and (Pd-BIA-PSi-Fe3O4)] was designed and used for the synthesis of di aryl ether by Ulmann cross-coupling reactions. Ulmann reaction performed with mixing of the arylhalides and phenol derivatives in DMF solvent. The prepared catalysts were characterized with various analytical techniques such as FT-IR, XRD, TGA, SEM, TEM, EDX, ICP and VSM. Pd-APM-PSi-Fe3O4 and Pd-BIA-PSi-Fe3O4 catalysts demonstrated good to excellent yields catalytic efficiency for Ulmann reactions in comparison with to commercial palladium catalysts. The catalyst is easily recycled and reused without loss of the catalytic activity. The combined merits of reusable catalyst conditions make the condensation with safe operation, no leaching of pd into environment, low pollution, rapid access to products and simple workup. Also, these novel magnetic nanocatalysts are superior to the industry standard Pd in every relevant aspect. They feature a way higher initial activity, a much more convenient separation, better recycling, and less contamination of the products. Last but not least, they can be very easily prepared from commercially available Fe3O4 nanoparticles using standard laboratory equipment.
- Chen, Jin,Dai, Linfang,Li, Jiayu,Mohammadnia, Majid
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- Preparation and characterization of isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe3O4 nanoparticles as a novel magnetic catalyst for the Ullmann coupling reaction
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Isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe3O4 nanoparticles (Cu-IS-AMBA-MNPs) as a new catalyst was designed, prepared and characterized by appropriate analyses. The heterogeneous reusable catalyst was successfully used for the efficient and widespread syntheses of diaryl ethers and diarylamines via the Ullmann coupling reaction. This green catalyst was easily removed, reused several times with no significant loss of its activity, and provided a clean synthesis with excellent yield and reduced time.
- Khodaei, Mohammad Mehdi,Alizadeh, Abdolhamid,Haghipour, Maryam
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p. 2727 - 2747
(2019/02/13)
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- Novel EDA transient electron donor-acceptor complex, and preparation method and applications thereof
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The invention relates to a novel EDA transient electron donor-acceptor complex, and a preparation method and applications thereof. The structure of the complex is represented in the description, wherein R1 represents an electron-withdrawing group such as cyano, nitro, acetyl, trifluoromethyl, and the like; R2 represents any one substituent group such as hydrogen, an alkyl group (methyl, ethyl, etc.), chlorine, bromine, iodine, methoxyl, nitro, and the like; and the position of the substituent group can be an o-position, m-position, or p-position. According to the synthesis method, under the induction of visible light, phenol derivatives and electron deficient aryl halide carry out reactions under the action of basic cesium carbonate to generate the complex, and no transition metal catalyst, transition metal ligand, or photo oxidation-reduction agent is added. Through the reaction mechanism, a series of diaryl ether derivatives is prepared. The preparation method has the advantages of mild conditions, greenness, high efficiency, low cost, and simple operation.
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Paragraph 0049-0052
(2019/07/04)
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- A diaryl ether compounds of the novel preparation method and application thereof
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The invention relates to a diaryl ether compounds of the novel preparation method, in particular compound is added to the reactor in sequence 1, dimethyl sulfoxide, cesium carbonate, compound 2, stirring at room temperature 10 - 60 minutes; then placing the reaction temperature is set to 70 - 120 °C the pot of the oil bath, and incandescent lamp for irradiation, the course of the reaction by TLC detection, to be after the reaction, the reaction solution by filtration, extraction and column chromatography, to obtain the target compound, the completion of the diaryl ether compound preparation. The technical scheme of the present invention visible under light induction, does not add any transition metal catalyst and ligand firmly oxidation reducing agent, aryl halide with phenol derivatives in photocatalytic C - O cross-coupling reaction. Preparation of mild conditions, green, high efficiency, low cost, simple and convenient operation. The preparation of this compound is a biological, medical, in the field of organic synthesis in particular pharmaceutical synthesis of important synthetic intermediate.
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Paragraph 0037-0040
(2019/07/01)
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- EDA (electronic design automation) transient electron donor-acceptor complex as well as preparation method and application thereof
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The invention relates to an EDA (electronic design automation) transient electron donor-acceptor complex as well as a preparation method and application thereof. The compound has a structural formulashown in the specification, in the formula, R1 is an electron withdrawing group such as cyan, nitryl, acetyl and trifluoromethyl; R2 is any one of arbitrary substituent groups such as hydrogen, methyl, ethyl and other alkyl groups, chloro, bromo, iodo, methoxyl and nitryl; and the position relationship of the substituent groups is any one of an ortho-position, a meta-position and a para-position.According to a synthesis method, under induction of visible light, without addition of any transition metal catalyst, ligand or photoredox agent, the complex is prepared from a phenol derivative and an electron-deficient aryl halide under the action of alkali cesium carbonate through reactions. In addition, a series of diaryl ether derivatives are prepared through the reaction mechanism. The condition is gentle and green, the efficiency is high, the cost is low and operation is simple and convenient.
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Paragraph 0043-0046
(2019/09/13)
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- Method for preparing diaryl ether compound
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The invention relates to a novel preparation method of a diaryl ether compound. The novel preparation method specifically comprises the following steps: sequentially putting a derivative of benzene, dimethyl sulfoxide, cesium carbonate and a phenol derivative into a reactor, and carrying out stirring for 30-60 minutes at room temperature; putting the mixture into an oil bath pot of which the reaction temperature is set as 70-120 DEG C, lighting the mixture with an incandescent light bulb, detecting the reaction process with TLC (thin layer chromatography), after the reaction is completed, carrying out filtering on a reaction liquid, and carrying out extraction and column chromatography, so as to obtain a target compound and complete preparation of the diaryl ether compound. By adopting thetechnical scheme of the invention, under induction of visible light, without addition of any transition metal catalyst, ligand or photoredox agent, an aryl halide and a phenol derivative are subjected to a photocatalytic C-O cross coupling reaction. The preparation method is mild in condition, green, efficient, low in cost and simple and convenient in operation. The prepared compound is a significant synthesis intermediate in fields such as biologics, medicines and organic synthesis, particularly in medicine synthesis.
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Paragraph 0038; 0039; 0040; 0041
(2019/09/13)
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- Ullmann Coupling Reaction of Nitro-Substituted Aryl Halides with Phenols under Mild Conditions: Micro-/Mesoporous Hierarchical LaAlPO-5 Zeolite Catalyst
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Heterogeneous catalytic reactions of aromatic organic molecules over zeolite catalysts present many challenges because of the shape selectivity of the micropores of conventional zeolites that limits the diffusion of aromatic molecules. Herein, Ullmann coupling reactions of phenols with nitro-substituted aryl halides were catalyzed by rare-earth-doped mesoporous AlPO-5 zeolites in the absence of ligands. The AlPO-5-MAlPO-5-M zeolites had a pure AFI structure and consisted of spherical particles assembled by nanofibers. The rare-earth elements were highly dispersed in the AlPO-5-MAlPO-5-M samples. The LaAlPO-5-MAlPO-5-M zeolite is an excellent catalyst for Ullmann coupling reactions of phenols and nitro-substituted aryl halides. Mesoporous LaAlPO-5 has an excellent stability and recyclability in the Ullmann coupling of p-X-nitrobenzene (X=Cl, Br, and I) with 2-naphthol. These results are important in the exploration of attractive Ullmann coupling reactions and in the development of mesoporous zeolite catalysts for other organic reactions.
- Ke, Qingping,Wu, Mingzhou,Wang, Chao,Lu, Guanzhong
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p. 1557 - 1563
(2016/05/02)
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- Discovery of 1,2,4-triazole-1,3-disulfonamides as dual inhibitors of mitochondrial complex II and complex III
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Respiratory chain succinate-ubiquinone oxidoreductase (SQR or complex II) and ubihydroquinone-cytochrome (cyt) c oxidoreductase (cyt bc1 or complex III) have been demonstrated as the promising targets of numerous antibiotics and fungicides. As a continuation of our research work on the development of new fungicides, a series of 1,2,4-triazole-1,3-disulfonamide derivatives with dual functions targeting both SQR and cyt bc1 were designed and synthesized by coupling diverse diphenyl ether moieties with triazolesulfonamide units. These newly synthesized compounds were characterized by elemental analyses, 1H NMR and ESI-MS spectrometry. The in vitro assay indicated that most of the synthesized compounds displayed good inhibition against porcine succinate-cytochrome reductase (SCR) with IC50 values ranging from 3.2 to 81.8 μM, revealing much higher activity than that of the commercial control amisulbrom whose IC50 value is 93.0 μM. Further evaluation against the respective SQR and cyt bc1 indicated that most compounds exhibited SQR-inhibiting activity as well as cyt bc1-inhibiting activity, but the inhibition potency against SQR is much higher than that against cyt bc1, showing that the SCR inhibition might be contributed greatly by the SQR inhibition. The further antibacterial evaluation against Xanthomonas oryzae pv. oryzae revealed that four compounds showed excellent potency at the concentration of 20 μg mL-1. In particular, compounds 6h and 6j exhibited much better antibacterial activity than the commercial control bismerthiazol in terms of their EC50. Impressively, 6j has an EC90 of 33.62 μg mL-1, more than 10-fold higher than that of bismerthiazol.
- Cheng, Hua,Shen, Yan-Qing,Pan, Xia-Yan,Hou, Yi-Ping,Wu, Qiong-You,Yang, Guang-Fu
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p. 7281 - 7292
(2015/09/02)
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- Betti base as an efficient ligand for copper-catalyzed ullmann coupling of phenol with aryl halides
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GRAPHICAL ABSTRACT A simple, general, and highly efficient Betti base ligand has been developed for copper-catalyzed Ullmann coupling of phenol with aryl halides without the protection of an inert atmosphere. The reaction proceeds smoothly in the presence of K2CO3 as the base and dimethylsulfoxide as the solvent. The catalyst was reused several times with no evident loss of catalytic activity and is environmentally friendly.
- Yang, Li,Yang, Qichao,Shi, Jianxin,Wang, Yufang,Zhang, Mingjie
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supporting information
p. 2468 - 2477
(2014/08/05)
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- Synthesis and properties of 1,3,4-oxadiazole-containing bismaleimides with asymmetric structure and the copolymerized systems thereof with 4,4′-bismaleimidodiphenylmethane
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Two novel bismaleimide monomers containing 1,3,4-oxadiazole and asymmetric structure, i.e., 2-[4-(4-maleimidophenoxy)phenyl]-5-(4-maleimidophenyl)-1,3,4- oxadiazole (p-Mioxd) and 2-[3-(4-maleimidophenoxy)phenyl]-5-(4-maleimidophenyl)- 1,3,4-oxadiazole (m-Mioxd), were designed and synthesized. The chemical structures of the monomers were confirmed using Fourier transform infrared spectroscopy (FTIR), 1H NMR and 13C NMR spectroscopy and elemental analysis. The thermal properties of the monomers were investigated by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). The results indicate that the incorporation of the 1,3,4-oxadiazole and asymmetric structure could improve the solubility and processability of the BMI monomers and the thermal stability of the resins. Composites composed of glass cloth and 4,4′-bismaleimidodiphenylmethane (BMDM), which were modified with 2.5, 5 and 10 wt% p-Mioxd and m-Mioxd, respectively, were also prepared. The TGA and DMA results demonstrate that the resulting composites have excellent thermal stability with high residual weight percentage at 700 °C (>45%) and Tg (>450 °C).
- Xia, Lianlian,Zhai, Xuejiao,Xiong, Xuhai,Chen, Ping
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p. 4646 - 4655
(2014/01/17)
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- Coupling of boronic acids with amines in the presence of a supported copper catalyst
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An efficient heterogeneous catalytic method was developed for Chan-Lam reaction, coupling of amines and boronic acid. Copper on 4 A molecular sieve provided yields comparable to the methods published. The method provides the main advantages of a heterogeneous catalytic procedure, the preparation of the catalyst is easy, the workup of the reaction mixture is simple. Graphical abstract: [Figure not available: see fulltext.]
- Debreczeni, Nora,Fodor, Anna,Hell, Zoltan
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p. 1547 - 1551,5
(2014/11/12)
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- First palladium-catalyzed denitrated coupling reaction of nitroarenes with phenols
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The first palladium-catalyzed protocol for the denitrated coupling reaction of nitroarenes with phenols has been developed, achieving unsymmetrical diaryl ethers in moderate to excellent yields. The cyclopalladated ferrocenylimine (catalyst Ic) exhibited highly catalytic activity for this transformation with low catalyst loading (0.75 mol%) and short reaction time (2 h). The efficiency of this reaction was demonstrated by its compatibility with a range of groups. Moreover, the rigorous exclusion of air or moisture was not required in these transformations. Copyright
- Wang, Hailei,Yu, Ajuan,Cao, Aijuan,Chang, Junbiao,Wu, Yangjie
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p. 611 - 614
(2013/10/21)
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- Chemo-selective copper-catalyzed C-O coupling reactions of phenols with aryl/vinyl halides using enaminone as efficient ligand
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The copper-catalyzed Ullmann C-O coupling reactions between phenols and aryl/vinyl halides have been efficiently performed by employing (E)-3-(dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-one, an easily available enaminone, as ligand. This new ligand is advantageous for its easy availability, broad applicability and good efficiency. Copyright 2012 John Wiley & Sons, Ltd. Copyright
- Wan, Jie-Ping,Wang, Chunping,Liu, Yunyun
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experimental part
p. 445 - 447
(2012/09/25)
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- Synthesis of glutamic acid analogs as potent inhibitors of leukotriene A4 hydrolase
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Leukotriene B4 (LTB4) is a potent pro-inflammatory mediator that has been implicated in the pathogenesis of multiple diseases, including psoriasis, inflammatory bowel disease, multiple sclerosis and asthma. As a method to decrease the level of LTB4 and possibly identify novel treatments, inhibitors of the LTB4 biosynthetic enzyme, leukotriene A4 hydrolase (LTA4-h), have been explored. Here we describe the discovery of a potent inhibitor of LTA4-h, arylamide of glutamic acid 4f, starting from the corresponding glycinamide 2. Analogs of 4f are then described, focusing on compounds that are both active and stable in whole blood. This effort culminated in the identification of amino alcohol 12a and amino ester 6b which meet these criteria.
- Kirkland, Thomas A.,Adler, Marc,Bauman, John G.,Chen, Ming,Haeggstroem, Jesper Z.,King, Beverly,Kochanny, Monica J.,Liang, Amy M.,Mendoza, Lisa,Phillips, Gary B.,Thunnissen, Marjolein,Trinh, Lan,Whitlow, Marc,Ye, Bin,Ye, Hong,Parkinson, John,Guilford, William J.
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p. 4963 - 4983
(2008/12/21)
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- Microwave-assisted construction of diaryl ethers directly from arylmethanesulfonates as convenient latent phenols with aryl halides
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The microwave-assisted synthesis of diaryl ethers directly from aryl halides and arylmethanesulfonates, which as latent phenols obviate a deprotection step prior to the SNAr reaction, in the presence of Cs2CO3 is described. The reaction time was very short (6-9-min), and good to excellent yields (53-90%) with the wide substrate scope were achieved without any catalyst. Copyright Taylor & Francis Group, LLC.
- Xu, Hui,Chen, Yang
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p. 2411 - 2420
(2008/02/10)
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- C(aryl)-O bond formation from aryl methanesulfonates via consecutive deprotection and SNAr reactions with aryl halides in an ionic liquid
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An efficient K3PO4-mediated synthesis of unsymmetrical diaryl ethers using the ionic liquid [Bmim]BF4 (1-butyl-3-methylimidazolium tetrafluoroborate) as solvent has been developed. The procedure involves consecutive deprotection of aryl methanesulfonates and a nucleophilic aromatic substitution (SNAr) with activated aryl halides.
- Xu, Hui,Chen, Yang
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p. 861 - 867
(2008/02/05)
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- Inhibitors of protein kinases
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Compounds that inhibit protein kinases, compositions containing the compounds and methods of treating diseases using the compounds are disclosed.
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Page/Page column 19
(2010/11/27)
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- A versatile and efficient ligand for copper-catalyzed formation of C-N, C-O, and P-C bonds: Pyrrolidine-2-phosphonic acid phenyl monoester
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A new and readily available bidentate ligand, namely, pyrrolidine-2- phosphonic acid phenyl monoester (PPAPM), has been developed for the copper-catalyzed formation of C-N, C-O, and P-C bonds, and various N-, O-, and P-arylation products were synthesized in good to excellent yields by using the CuI/PPAPM catalyst system. Addition of the PPAPM ligand greatly increases the reactivity of the copper catalyst, and the resulting versatile and efficient catalyst system is of widespread and practical application in cross-coupling reactions.
- Rao, Honghua,Jin, Ying,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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p. 3636 - 3646
(2008/02/03)
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- Dimethylaminomethylphosphonic acid derivatives-promoted CuI-catalyzed synthesis of aryl ethers
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An inexpensive and efficient catalyst system for synthesis of aryl ethers has been developed by using 20 mol% CuI as the catalyst, 30 mol% dimethylaminomethylphosphonic acid derivatives as the new ligands, K 2CO3 as the base and toluene as the solvent. This is the first example using aminophosphonates as the ligands for Ullmann ether coupling reaction. Georg Thieme Verlag Stuttgart.
- Jin, Ying,Liu, Jinyong,Yin, Yingwu,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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p. 1564 - 1568
(2007/10/03)
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- NOVEL HETEROCYCLIC AMIDE DERIVATIVES HAVING DIHYDROOROTATE DEHYDROGENASE INHIBITING ACTIVITY
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Novel heterocyclic amide derivatives having pharmacological effects, that is, compounds represented by the general formula (1) or salts thereof: (1) wherein X1-X2 is S-CH2 or the like; R1 is alkyl or the like; p is 0 to 7; R2 is hydrogen, alkyl, or the like; R3 is hydrogen, alkyl, or the like; Y1-Y2 is CH=CH or the like; R4 is halogeno, alkyl, or the like; q is 0 to 4; and R5 is halogeno, hydrogen, alkyl, or the like.
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Page/Page column 43
(2010/10/20)
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- Derivatives of quinoline as inhibitors for MEK
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1. A compound of formula (I) or a pharmaceutically acceptable salt thereof. wherein: n is 0-1; X and Y are independently selected from -NH-, -O-, -S-, or -NR8- where R8 is alkyl of 1-6 carbon atoms and X may additionally comprise a CH2 group; R7 is a group (CH2)mR9 where m is 0,or an integer of from 1-3 and R9 is a substituted aryl group, an optionally substituted cycloalkyl ring of up to 10 carbon atoms, or an optionally substituted heterocyclic ring or an N-oxide of any nitrogen containing ring; R6 is a divalent cycloalkyl of 3 to 7 carbon atoms, which may be optionally further substituted with one or more alkyl of 1 to 6 carbon atom groups; or is a divalent pyridinyl, pyimidinyl, or phenyl ring; wherein the pyridinyl, pyrimidinyl, or phenyl ring may be optionally further substituted with one or more specified groups; R1, R2, R3 and R4 are each independently selected from hydrogen or various specified organic groups. Compounds are useful as pharmaceuticals for the inhibition of MEK activity.
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Page/Page column 78
(2010/02/14)
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- Microwave assisted aromatic nucleophilic substitution reaction under solventless condition
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We report here microwave assisted aromatic nucleophilic substitution reaction of 1-chloro-4-nitrobenzene with different phenoxides.
- Rebeiro, Geeta L.,Khadilkar, Bhushan M.
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p. 1405 - 1410
(2007/10/03)
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- Synthesis of substituted benzyl 2-methyl-2-phenylpropyl ethers and their moth-proofing activity on wool against larvae of Anthrenus fasciatus
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Synthesis of new moth-proofing agents is necessary to overcome the damage caused by clothes moths and carpet beetles to hosiery and upholstery. In the present paper substituted benzyl 2-methyl-2-phenylpropyl ethers were synthesised and evaluated for moth-proofing activity. Two compounds were found to provide protection against larvae of Anthrenus fasciatus at levels of 1.0 and 10 g kg-1 respectively. The introduction of a methyl group in the para position of the benzene ring attached to C2 of the 2-methylpropyl chain (ring A) increased moth-proofing activity. The introduction of a phenoxy ring at the meta position of the benzyl nucleus (ring B) also increased activity, while the presence of a nitro group on the benzyl nucleus (ring B) decreased activity.
- Acharya,Joshi
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p. 850 - 856
(2007/10/03)
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- Halopyridyl triazolinone herbicides and herbicidal use thereof
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Disclosed are herbicidal halopyridyl triazolinones, herbicidal compositions comprising the halopyridyl triazolinones, and herbicidal use of the compounds and compositions. Such compounds and compositions are useful as both preemergence and postemergence herbicides in a variety of crops.
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- Diarylether inhibitors of farnesyl-protein transferase
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The design and synthesis of simple nonpeptide inhibitors of farnesyl-protein transferase (FTase) are described. Cysteine-derived diarylether frameworks are appropriate structural replacements for the C-terminal tetrapeptide portion of the Ras protein, and possess in vitro potency against FTase. Inhibitory activity is dependent on the ring-substitution pattern, and does not require the presence of a C-terminal carboxylate group.
- Dinsmore, Christopher J.,Williams, Theresa M.,Hamilton, Kelly,O'Neill, Timothy J.,Rands, Elaine,Koblan, Kenneth S.,Kohl, Nancy E.,Gibbs, Jackson B.,Graham, Samuel L.,Hartman, George D.,Oliff, Allen I.
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p. 1345 - 1348
(2007/10/03)
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- Process of improving activity of herbicides and fertilizers using N-(2-hydroxyethyl)-acetamide or -propanamide
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The invention is related to the use of certain water-soluble compounds known as such and having the Formula for the modulation of membrane dependent metabolism processes within living cells, in particular with relation to transport phenomena and cell procedures which are induced or influenced by active agents supplied from outside the cell, products containing these substances for the above described uses and processes using these products.
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