- Copper pyrithione (CuPT)-catalyzed/mediated amination and thioarylation of (hetero)aryl halides: A competition
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A facile method for the synthesis of N-arylheterocycles and di(hetero)aryl sulfides under mild condition is described. In these transformations, copper pyrithione (CuPT) was used as the copper catalyst for C─N coupling, while served as catalyst and coupled partner for C─S coupling with high yields and broad substrate tolerance. The S-arylation process was also utilized for the construction of valuable bioactive 2-sulfonylpyridine 1-oxide derivatives.
- Cao, Ningtao,Song, Bao,Xie, Jianwei,Zhang, Jie
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- ORGANOMETALLIC COMPOUND AND ORGANIC LIGHT-EMITTING DEVICE INCLUDING THE SAME
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An organic light-emitting device includes an organometallic compound represented by M1(L1)n1(L2)n2, wherein L1 is a ligand represented by Formula 1-1: In Formula 1-1, *1 to *4 indicate a bi
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Paragraph 0433; 0434
(2020/06/15)
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- GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE
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Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with a defect in glyoxylate metabolism, for example a disease or disorder associated with the enzyme glycolate oxidase (GO) or alterations in oxalate metabolism. Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.
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Paragraph 002089; 002090
(2021/01/22)
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- Electrophotocatalysis with a Trisaminocyclopropenium Radical Dication
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Visible-light photocatalysis and electrocatalysis are two powerful strategies for the promotion of chemical reactions. Here, these two modalities are combined in an electrophotocatalytic oxidation platform. This chemistry employs a trisaminocyclopropenium (TAC) ion catalyst, which is electrochemically oxidized to form a cyclopropenium radical dication intermediate. The radical dication undergoes photoexcitation with visible light to produce an excited-state species with oxidizing power (3.33 V vs. SCE) sufficient to oxidize benzene and halogenated benzenes via single-electron transfer (SET), resulting in C?H/N?H coupling with azoles. A rationale for the strongly oxidizing behavior of the photoexcited species is provided, while the stability of the catalyst is rationalized by a particular conformation of the cis-2,6-dimethylpiperidine moieties.
- Huang, He,Strater, Zack M.,Rauch, Michael,Shee, James,Sisto, Thomas J.,Nuckolls, Colin,Lambert, Tristan H.
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supporting information
p. 13318 - 13322
(2019/08/12)
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- Ni-Catalyzed Reductive Cyanation of Aryl Halides and Phenol Derivatives via Transnitrilation
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Herein, we report a Ni-catalyzed reductive coupling for the synthesis of benzonitriles from aryl (pseudo)halides and an electrophilic cyanating reagent, 2-methyl-2-phenyl malononitrile (MPMN). MPMN is a bench-stable, carbon-bound electrophilic CN reagent that does not release cyanide under the reaction conditions. A variety of medicinally relevant benzonitriles can be made in good yields. Addition of NaBr to the reaction mixture allows for the use of more challenging aryl electrophiles such as aryl chlorides, tosylates, and triflates. Mechanistic investigations suggest that NaBr plays a role in facilitating oxidative addition with these substrates.
- Mills, L. Reginald,Graham, Joshua M.,Patel, Purvish,Rousseaux, Sophie A. L.
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supporting information
p. 19257 - 19262
(2019/12/02)
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- COMPOUNDS FOR USING IN IMAGING AND PARTICULARLY FOR THE DIAGNOSIS OF NEURODEGENERATIVE DISEASES
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The invention relates to compounds of formula (II) for using in imaging and particularly for the diagnosis of neurodegenerative diseases
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Paragraph 0913; 0914
(2019/07/23)
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- GLYCOLATE OXIDASE INHIBITORS FOR THE TREATMENT OF DISEASE
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Described herein are compounds, methods of making such compounds, pharmaceutical compositions and medicaments containing such compounds, and methods of using such compounds to treat or prevent diseases or disorders associated with the enzyme glycolate oxidase (GO). Such diseases or disorders include, for example, disorders of glyoxylate metabolism, including primary hyperoxaluria, that are associated with production of excessive amounts of oxalate.
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Paragraph 002131; 002132; 002133
(2019/07/17)
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- Benzothiadiazole-Based Small-Molecule Semiconductors for Organic Thin-Film Transistors and Complementary-like Inverters
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New benzothiadiazole derivatives, 4,7-bis(5-phenylthiophen-2-yl)benzo[c][1,2,5]thiadiazole (PT-BTD) and 4,7-bis[4-(thiophen-2-yl)phenyl]benzo[c][1,2,5]thiadiazole (TP-BTD), were synthesized and characterized as small-molecule organic semiconductors for organic thin-film transistors (OTFTs) and complementary inverters. The thermal, optical, and electrochemical properties of the new compounds were fully characterized. Vacuum-deposition and solution-shearing methods were used to fabricate thin films based on these compounds. Thin films based on PT-BTD exhibited p-channel characteristics with hole mobilities as high as 0.10 cm2 V?1 s?1 and current on/off ratios >107 for top-contact/bottom-gate OTFT devices. With an optimized blending ratio of PT-BTD and the representative n-channel semiconductor N,N′-1H,1H-perfluorobutyl dicyanoperylenediimide, bulk heterojunction ambipolar transistors were fabricated with balanced hole and electron mobilities of 0.10 and 0.07 cm2 V?1 s?1, respectively. Furthermore, a complementary-like inverter was fabricated using ambipolar thin-film transistors, which showed a high voltage gain of 84.
- Kim, Hyekyoung,Reddy, M. Rajeshkumar,Kim, Hyungsug,Choi, Donghee,Kim, Choongik,Seo, SungYong
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p. 742 - 749
(2017/06/06)
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- Ruthenium-Catalyzed meta-Selective C?H Mono- and Difluoromethylation of Arenes through ortho-Metalation Strategy
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The first example for the ruthenium-catalyzed ligand-directed meta-selective C?H mono- and difluoromethylation is developed, affording a variety of new meta-mono- and difluoromethylated 2-phenylpyridines, 2-phenylpyrimidines, and 1-phenylpyrazoles in moderate-to-good yields. This new transformation exhibits broad substrate scope, good functional group tolerance, and high efficiency, and offers a practical approach to synthesize mono- and difluoromethylated arenes. Mechanistic studies indicate that a reaction pathway involving palladium-initiated radical species is involved in the catalytic cycle. The new dual catalytic system consisting of compatible ruthenium(II) and palladium(0) complexes enables the key processes of C?H activation and mono-/difluoromethyl-radical formation to occur and achieves the meta-selective functionalization efficiently. In addition, the present protocol can also be extended to non-fluoromethylation.
- Li, Zhong-Yuan,Li, Liang,Li, Qi-Li,Jing, Kun,Xu, Hui,Wang, Guan-Wu
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supporting information
p. 3285 - 3290
(2017/03/16)
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- BIARYL DERIVATIVE AS GPR120 AGONIST
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The present invention relates to a biaryl derivative expressed by the chemical formula 1, a method for producing the biaryl derivative, a pharmaceutical composition comprising same, and use of same, the biaryl derivative expressed by the chemical formula 1, as a GPR120 agonist, promoting GLP-1 generation in the gastro-intestinal tract, reducing insulin resistance in the liver, muscles and the like from anti-inflammatory activity in the macrophage, pancreatic cells and the like, and allowing effective use in prevention or treatment of inflammation or metabolic diseases such as diabetes, complications from diabetes, obesity, non-alcoholic fatty liver disease, fatty liver disease, and osteoporosis.
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Paragraph 0217
(2017/11/17)
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- NITROGEN-CONTAINING HETEROCYCLIC COMPOUND
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The present invention provides a compound having a cholinergic muscarinic M1 receptor positive allosteric modulator activity and useful as a medicament such as a prophylactic or therapeutic drug for Alzheimer's disease, schizophrenia, pain, sleep disorder, Parkinson's disease dementia, dementia with Lewy bodies and the like, and the like. The present invention relates to a compound represented by the formula (I) or a salt thereof. wherein each symbol is as described in the attached DESCRIPTION.
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Paragraph 0278
(2017/08/01)
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- HETEROCYCLIC MODULATORS OF LIPID SYNTHESIS AND COMBINATIONS THEREOF
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Heterocyclic modulators of lipid synthesis are provided as well as pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising such compounds; and methods of treating conditions characterized by disregulation of a fatty acid synthase pathway by the administration of such compounds and combinations of such compounds and other therapeutic agents.
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Page/Page column 157; 158
(2015/07/07)
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- HETEROCYCLIC MODULATORS OF LIPID SYNTHESIS
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Heterocyclic modulators of lipid synthesis are provided as well as pharmaceutically acceptable salts thereof; pharmaceutical compositions comprising such compounds; and methods of treating conditions characterized by disregulation of a fatty acid synthase pathway by the administration of such compounds.
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Page/Page column 142; 143
(2014/01/18)
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- 3-(Diphenylphosphino)propanoic acid: An efficient ligand for the Cu-catalyzed N-arylation of imidazoles and 1H-pyrazole with aryl halides
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3-(Diphenylphosphino)propanoic acid (L2) has proved to be an efficient ligand for the copper-catalyzed CN coupling reactions. N-arylation of imidazoles with aryl iodides catalyzed by CuCl/L2 was smoothly carried out in DMSO at 100 °C with a yield up to 98%. N-arylation of 1H-pyrazole with aryl iodides and bromides catalyzed by Cu(OAc)2/L2 in 1,4-dioxane also gave the corresponding products with yields of 40%-98%.
- Liu, Ya-Shuai,Liu, Yan,Ma, Xiao-Wei,Liu, Ping,Xie, Jian-Wei,Dai, Bin
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p. 775 - 778
(2014/06/09)
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- Copper-catalyzed arylation of nitrogen heterocycles from anilines under ligand-free conditions
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The arylation of pyrazole and derivatives can be achieved by coupling arenediazonium species (formed in situ from anilines) by using a catalytic system that employs low-toxicity and inexpensive copper metal under very mild and ligand-free conditions (T = 20 ° C). From other nitrogen heterocycles, the presence of an additive (NBu4I) significantly improves the efficiency of the catalytic system. These results represent the first examples of C-N bond formation from arenediazonium species.
- Toummini, Dounia,Tlili, Anis,Bergs, Julien,Ouazzani, Fouad,Taillefer, Marc
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supporting information
p. 14619 - 14623
(2015/01/09)
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- Salen-Cu(II) complex catalysed N-arylation of pyrazole under mild conditions
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Three inexpensive and air-/moisture-stable complexes (Salden)Cu (Salden = N, N'-bis(salicylidene)-1,2-dimethylethylenediamine), (Saldch)Cu (Saldch = N, N'-bis(salicylidene)-1,2-cyclohexenediamine), and (Salph)Cu (salph = N, N'-bis(salicylidene)-1,2-phenylenediamine) were synthesised and evaluated as catalysts for the N-arylation of pyrazole with aryl halides. A variety of aryl iodides and bromides underwent coupling with pyrazole, promoted by the (Saldch)Cu complex, in moderate to excellent yields without the protection by an inert gas.
- Liu, Yan,Liu, Wei,Zhang, Qin,Liu, Ping,Xie, Jian-Wei,Dai, Bin
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p. 636 - 637
(2013/11/06)
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- Catalyst-free N-arylation using unactivated fluorobenzenes
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Caught in a 'SNAr'e: A one-step, high-yielding, catalyst-free method is described for N-arylation of azoles and indoles from unactivated monofluorobenzenes. This SNAr reaction tolerates a wide range of substituents and can also generate halogenated N-aryl products. The reaction can also be performed simultaneously with or subsequent to a copper- or palladium-catalyzed cross-coupling reaction in the same pot. Copyright
- Diness, Frederik,Fairlie, David P.
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supporting information; experimental part
p. 8012 - 8016
(2012/09/05)
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- A manganese/copper bimetallic catalyst for C-N coupling reactions under mild conditions in water
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An efficient and convenient bimetallic MnF2/CuI catalyst in combination with trans-1,2-diaminocyclohexane has been developed for the cross-coupling of nitrogen heterocycles with aryl halides in water at moderate temperature. A variety of nitrogen nucleophiles including pyrazole, 7-azaindole, indazole, indole, pyrrole and imidazole afforded the corresponding products in moderate to good yields (up to 94%) under the described arylation conditions.
- Teo, Yong-Chua,Yong, Fui-Fong,Lim, Gina Shiyun
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supporting information; experimental part
p. 7171 - 7174
(2012/01/05)
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- Ligands for copper-catalyzed C-N bond forming reactions with 1 Mol% CuBr as catalyst
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Several new ligands were designed to promote copper-catalyzed Ullman C-N coupling reactions. In this group, 8-hydroxyquinolin-N-oxide was found to serve as a superior ligand for CuBr-catalyzed coupling reactions of aryl iodides, bromides, and chlorides with aliphatic amines and N-heterocycles under a low catalyst loading (1% [Cu] mol). Reactions with the inexpensive catalytic system display a high functional group tolerance as well as excellent chemoselectivity.
- Yang, Kai,Qiu, Yatao,Li, Zheng,Wang, Zhaoyang,Jiang, Sheng
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experimental part
p. 3151 - 3159
(2011/06/23)
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- Complete assignment of NMR data of 22 phenyl-1H-pyrazoles' derivatives
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Complete assignment of 1H and 13C NMR chemical shifts and J(1H/1H and 1H/19F) coupling constants for 22 1-phenyl-1H-pyrazoles' derivates were performed using the concerted application of 1H 1D and 1H, 13C 2D gs-HSQC and gs-HMBC experiments. All 1-phenyl-1H-pyrazoles' derivatives were synthesized as described by Finar and co-workers. The formylated 1-phenyl-1H-pyrazoles' derivatives were performed under Duff's conditions. Copyright
- De Oliveira, Aline Lima,Alves De Oliveira, Carlos Henrique,Mairink, Laura Maia,Pazini, Francine,Menegatti, Ricardo,Liao, Luciano Morais
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scheme or table
p. 537 - 542
(2011/10/09)
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- Efficient cross-coupling reactions of nitrogen nucleophiles with aryl halides in water
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A facile and practical strategy has been developed for the N-arylation of nitrogen nucleophiles with aryl halides catalyzed by a combination of iron(III) chloride [FeCl3] and dimethylethylenediamine (dmeda) in water. A variety of nitrogen nucleophiles including pyrazole, indole, 7-azaindole and benzamide afforded the N-arylated products in the presence of the catalytic system (in up to 88% yield).
- Teo, Yong-Chua
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supporting information; experimental part
p. 720 - 724
(2009/11/30)
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- Manganese-catalyzed cross-coupling reactions of nitrogen nucleophiles with aryl halides in water
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A facile and convenient strategy for the assembly of N-arylated heterocycles has been demonstrated using a MnCl2·4H 2O/trans-1,2-diaminocyclohexane catalyst and K3PO 4 as the base in water.
- Teo, Yong-Chua,Yong, Fui-Fong,Poh, Chai-Yun,Yan, Yaw-Kai,Chua, Guan-Leong
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supporting information; experimental part
p. 6258 - 6260
(2010/02/16)
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- Method of forming a carbon-carbon or carbon-heteroatom linkage
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The invention relates to a method of creating a carbon-carbon or carbon-heteroatom linkage by reacting an unsaturated compound bearing a leaving group and a nucleophilic compound. More specifically, the invention relates to the creation of a carbon-nitrogen linkage involving the arylation of nitrogenous organic derivatives. The inventive method consists in creating a carbon-carbon or carbon-heteroatom linkage by reacting an unsaturated compound bearing a leaving group and a nucleophilic compound providing a carbon atom or a heteroatom (HE) capable of being substituted for the leaving group, thereby creating a C—C or C-HE linkage. The invention is characterised in that the reaction is carried out in the presence of an effective quantity of a catalyst based on copper and at least one ligand comprising at least one imine function and at least one additional nitrogen atom as chelating atoms
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Page/Page column 23; 25
(2010/02/14)
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- Mild conditions for copper-catalysed N-arylation of pyrazoles
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Copper-catalysed N-arylation of pyrazoles with aryl or heteroaryl bromides or iodides, which can include functional substituents, was performed under the mildest conditions yet described, with excellent yields and selectivity, by the use as catalyst of a combination of cuprous oxide with a set of inexpensive, chelating oxime-type ligands not previously known to promote such reactions. Other original bi-, tri- or tetradentate ligands providing nitrogen and/or oxygen as chelating atoms were also successfully tested in this type of arylation. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004).
- Cristau, Henri-Jean,Cellier, Pascal P.,Spindler, Jean-Francis,Taillefer, Marc
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p. 695 - 709
(2007/10/03)
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- Process for arylating or vinylating or alkynating a nucleophilic compound
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The present invention concerns a process for arylating or vinylating or alkynating a nucleophilic compound. More particularly, the invention concerns arylating nitrogen-containing organic derivatives. The arylating or vinylating or alkynating process of the invention consists of reacting a nucleophilic compound with a compound carrying a leaving group and is characterized in that the reaction is carried out in the presence of an effective quantity of a catalyst based on a metallic element M selected from groups (VIII), (Ib) and (IIb) of the periodic table and at least one ligand comprising at least one imine function and at least one supplemental nitrogen atom as the chelating atoms.
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