- Mild, General, and Regioselective Synthesis of 2-Aminopyridines from Pyridine N -Oxides via N -(2-Pyridyl)pyridinium Salts
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A synthesis of 2-aminopyridines from pyridine N-oxides via their corresponding N-(2-pyridyl)pyridinium salts has been demonstrated and investigated. The reaction sequence features a highly regioselective conversion of the N-oxide into its pyridinium salt
- Xiong, Hui,Hoye, Adam T.
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supporting information
p. 371 - 375
(2022/01/27)
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- Discovery and in Vivo Anti-inflammatory Activity Evaluation of a Novel Non-peptidyl Non-covalent Cathepsin C Inhibitor
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Cathepsin C (Cat C) participates in inflammation and immune regulation by affecting the activation of neutrophil serine proteases (NSPs). Therefore, cathepsin C is an attractive target for treatment of NSP-related inflammatory diseases. Here, the complete discovery process of the first potent "non-peptidyl non-covalent cathepsin C inhibitor"was described with hit finding, structure optimization, and lead discovery. Starting with hit 14, structure-based optimization and structure-activity relationship study were comprehensively carried out, and lead compound 54 was discovered as a potent drug-like cathepsin C inhibitor both in vivo and in vitro. Also, compound 54 (with cathepsin C Enz IC50 = 57.4 nM) exhibited effective anti-inflammatory activity in an animal model of chronic obstructive pulmonary disease. These results confirmed that the non-peptidyl and non-covalent derivative could be used as an effective cathepsin C inhibitor and encouraged us to continue further drug discovery on the basis of this finding.
- Chen, Xing,Yan, Yaoyao,Zhang, Zhaoyan,Zhang, Faming,Liu, Mingming,Du, Leran,Zhang, Haixia,Shen, Xiaobao,Zhao, Dahai,Shi, Jing Bo,Liu, Xinhua
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p. 11857 - 11885
(2021/09/02)
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- Synthesis of 2-guanidinyl pyridines and their trypsin inhibition and docking
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A range of guanidine-based pyridines, and related compounds, have been prepared (19 examples). These compounds were evaluated in relation to their competitive inhibition of bovine pancreatic trypsin. Results demonstrate that compounds in which the guanidinyl substituent can form an intramolecular hydrogen bond (IMHB) with the pyridinyl nitrogen atom (6a–p) are better trypsin inhibitors than their counterparts (10–13) that are unable to form an IMHB. Among the compounds 6a–p, examples containing a 5-halo substituent were, generally, found to be better trypsin inhibitors. This trend was inversely related to electronegativity, thus, 1-(5-iodopyridin-2-yl)guanidinium ion 6e (Ki = 0.0151 mM) was the optimum inhibitor in the 5-halo series. Amongst the isomeric methyl substituted compounds, 1-(3-methylpyridin-2-yl)guanidinium ion 6h demonstrated optimum levels of trypsin inhibition (Ki = 0.0140 mM). In order to rationalise the measured enzyme inhibition, selected compounds were docked with bovine and human trypsin with a view to understanding active site occupancy and taken together with the Ki values the order of inhibitory ability suggests that the 5-halo 2-guanidinyl pyridine inhibitors form a halogen bond with the catalytically active serine hydroxy group.
- Ahmed Al-Hadhrami, Nahlah,Evans, Paul,Ladwig, Angelique,Paul G. Malthouse, J.,Rahman, Adeyemi,Rozas, Isabel
-
supporting information
(2020/07/10)
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- Recyclable Pd/CuFe2O4 nanowires: A highly active catalyst for C-C couplings and synthesis of benzofuran derivatives
-
Pd/CuFe2O4 nanowire-catalyzed cross coupling transformations are described. Notably, these reactions showed excellent functional group tolerance. Further, the protocol is applied to a one-pot synthesis of benzofurans via a Sonogashira coupling and intramolecular etherification sequence. The catalyst was reused and found to maintain its activity and stability.
- Lakshminarayana, Bhairi,Chakraborty, Jhonti,Satyanarayana,Subrahmanyam, Ch.
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p. 21030 - 21039
(2018/06/13)
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- PROCESS FOR THE CATALYTIC DIRECTED CLEAVAGE OF AMIDE-CONTAINING COMPOUNDS
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The present invention relates to a catalytic method for the conversion of amide-containing compouds by means of a build-in directing group and upon the action of a heteronucleophilic compound (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or a thiol (RSH)) in the presence of a metal catalyst to respectively esters, thioesters, carbonates, thiocarbonates and to what is defined as amide-containing compounds (such as carboxamides, urea, carbamates, thiocarbamates). The present invention also relates to these amide-containing compounds having a build-in directing group (DG), as well as the use of such directing groups in the catalytic directed cleavage of N-DG amides with the use of heteronucleophiles (in se an amine (RNH2 or RNHR') or an alcohol (ROH) or thiol (RSH)).
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Page/Page column 51; 54
(2017/04/11)
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- METHODS FOR EXTERNAL BASE-FREE SUZUKI COUPLINGS
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The present disclosure describes a method of coupling a first aromatic compound to a second aromatic compound, the method comprising: (a) preparing a reaction mixture comprising the first aromatic compound, the second aromatic compound, a catalyst and water; the reaction mixture does not contain an external base, the reaction mixture having an initial pH of from 11 to 1; the catalyst having at least one group 10 atom; the first aromatic compound having a halogen, triflate or sulfonate substituent; the second aromatic compound having a boron-containing substituent; wherein, at least one of the first aromatic compound or the second aromatic compound includes one or more heteroatom; and (b) reacting the first aromatic compound and the second aromatic compound in the reaction mixture, the reaction mixture having a final pH following reaction of the first aromatic compound and the second aromatic compound.
- -
-
Paragraph 0040-0041
(2017/07/14)
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- One-Pot Palladium-Catalyzed Cross-Coupling Treble of Borylation, the Suzuki Reaction and Amination
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A methodology for a sequential palladium-catalyzed cross-coupling procedure consisting of borylation, the Suzuki reaction and amination has been developed for the assembly of molecules with multi-aryl backbones. The linchpin of this development is the meta-terarylphosphine ligand, Cy*Phine, which has been employed as an air- and moisture-stable precatalyst, Pd(Cy*Phine)2Cl2, to improve the efficiency of one-pot borylation–Suzuki reactions. Additionally, the reactivity of the Pd-Cy*Phine system could be tuned to furnish a one-pot, borylation–Suzuki reaction–amination (BSA) cross-coupling treble. The methodology successfully integrated complementary conditions for three distinctly different and modular reactions. Average yields of 74–94% could be achieved for each segment that cumulatively afforded 50–84% yield over the entire three-step sequence in a single pot. (Figure presented.).
- Jong, Howard,Eey, Stanley T.-C.,Lim, Yee Hwee,Pandey, Sangeeta,Iqbal, Nurul Azmah Bte,Yong, Fui Fong,Robins, Edward G.,Johannes, Charles W.
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supporting information
p. 616 - 622
(2017/02/23)
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- Pd-Catalyzed Suzuki coupling reactions of aryl halides containing basic nitrogen centers with arylboronic acids in water in the absence of added base
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The Pd-catalyzed Suzuki coupling reactions of a series of aryl chlorides and aryl bromides containing basic nitrogen centers with arylboronic acids in water in the absence of added base are reported. The reactions proceed either partially or entirely under acidic conditions. After surveying twenty-two phosphorus ligands, high yields of products were obtained with aryl chlorides only when a bulky ligand, 2-(di-tert-butyl-phosphino)-1-phenyl-1H-pyrrole (cataCXiumPtB) was used. In contrast, aryl bromides produced high yields of products in the absence of both added base and added ligand. In order to explore the Suzuki coupling process entirely under acidic conditions, a series of reactions were conducted in buffered acidic media using several model substrates. 4-Chlorobenzylamine, in the presence of cataCXiumPtB, produced high yields of product at buffered pH 6.0; the yields dropped off precipitously at buffered pH 5.0 and lower. The fall-off in yield was attributed to the decomposition of the Pd-ligand complex due to the protonation of the ligand in the more acidic aqueous media. In contrast, in the absence of an added ligand, 4-amino-2-chloropyridine produced quantitative yields at buffered pH 3.5 and 4.5 while 4-amino-2-bromopyridine produced quantitative yields in a series of buffered media ranging from pH 4.5 to 1.5. These substrates are only partially protonated in acidic media and can behave as active Pd ligands in the Suzuki catalytic cycle.
- Li, Zhao,Gelbaum, Carol,Campbell, Zachary S.,Gould, Paul C.,Fisk, Jason S.,Holden, Bruce,Jaganathan, Arvind,Whiteker, Gregory T.,Pollet, Pamela,Liotta, Charles L.
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supporting information
p. 15420 - 15432
(2017/12/15)
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- Novel cyclodextrin-modified h-BN@Pd(II) nanomaterial: An efficient and recoverable catalyst for ligand-free C-C cross-coupling reactions in water
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An environmentally friendly palladium(II) catalyst supported on cyclodextrin-modified h-BN was successfully prepared. The catalyst was characterized by FT-IR, SEM, TG, XRD and XPS, and the loading level of Pd in h-BN@β-CD@Pd(II) was measured to be 0.088?mmol g?1 by ICP. It exhibits excellent catalytic activity for the Suzuki and Heck reactions in water, and can be easily separated and consecutively reused for at least nine times. In addition, a series of pharmacologically interesting products were successfully synthesized using this catalyst to demonstrate its potential applications in pharmaceutical industries. Above all, this work opens up an interesting and attractive avenue for the use of cyclodextrin-functionalized h-BN as an efficient support for hydrophilic heterogeneous catalysts.
- Ma, Xiaojun,Lv, Guanghui,Cheng, Xu,Li, Weijian,Sang, Rui,Zhang, Yong,Wang, Qiantao,Hai, Li,Wu, Yong
-
-
- Ligand-Free C–C Coupling Reactions Promoted by Hexagonal Boron Nitride-Supported Palladium(II) Catalyst in Water
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A micron-scale palladium(II) material has been successfully prepared using Schiff base-modified hexagonal boron nitride as a support and used for the first time as an efficient and recyclable catalyst in organic synthesis. The morphology, composition, metal loading and thermal stability of the catalyst were studied using scanning electron microscopy (SEM), X-ray photoelectron spectroscopy (XPS), X-ray diffraction (XRD), infrared spectroscopy (FT-IR), inductively coupled plasma (ICP) and thermogravimetric (TG) analyses. Then, the micron material was tested in various C–C cross-coupling reactions and exhibited excellent catalytic activities in the Suzuki and Heck reactions. Moreover, the catalyst could be easily recovered by simple filtration and reused at least ten times without significant loss of its catalytic activity. In general, this work demonstrates the possibility of using Schiff-base@hexagonal boron nitride as an efficient support for heterogeneous catalysts. (Figure presented.).
- Cheng, Xu,Li, Weijian,Nie, Ruifang,Ma, Xiaojun,Sang, Rui,Guo, Li,Wu, Yong
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supporting information
p. 454 - 466
(2017/02/10)
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- Synthesis and evaluation of the anticoccidial activity of trifluoropyrido[1,2-a]pyrimidin-2-one derivatives
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Screening of our chemical library to discover new molecules exhibiting in vitro activity against the invasion of host cells by Eimeria tenella revealed a lead compound with an IC50 of 15 μM. Structure-activity relationship studies were conducted with 34 newly synthesized compounds to identify more active molecules and enhance in vitro activity against the parasite. Four compounds were more effective in inhibiting MDBK cell invasion in vitro than the lead compound.
- Silpa, Laurence,Niepceron, Alisson,Laurent, Fabrice,Brossier, Fabien,Pénichon, Mélanie,Enguehard-Gueiffier, Cécile,Abarbri, Mohamed,Silvestre, Anne,Petrignet, Julien
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p. 114 - 120
(2015/12/18)
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- An efficient water-soluble surfactant-type palladium catalyst for Suzuki cross-coupling reactions in pure water at room temperature
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A palladium catalyst based on a bidentate phosphine-type zwitterionic surfactant as a ligand exhibited an excellent catalytic activity in the Suzuki-Miyaura cross coupling reactions. This novel method allowed the reaction of aryl halides with arylboronic acids to occur in pure water at room temperature, forming a variety of biaryls in good to high yields. Heterobiaryls were also efficiently assembled even in the presence of water-insoluble heteroaryl halides as substrates. In addition, such a coupling protocol was successfully used in the iterative diarylation of 2,5-dibromopyridine in one-pot.
- Qiu, Pei,Zhao, Jing Yang,Shi, Xu,Duan, Xin Hong
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supporting information
p. 6568 - 6572
(2016/08/10)
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- Novel bis(benzothiazole-oxime)-based Pd(II)-complex: synthesis, characterization, quantum chemical calculations, and catalytic significance in Suzuki–Miyaura and Heck–Mizoroki cross coupling reactions
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Abstract: In the present work, a novel binuclear benzothiazole-oxime Pd(II) complex was synthesized, characterized (elemental analysis, infrared spectroscopy, thermogravimetric analysis, ultraviolet–visible spectroscopy, nuclear magnetic resonance, and conductance measurements), and explored for its catalytic activity in Suzuki–Miyaura and Heck–Mizoroki cross-coupling reactions of different aryl- and heteroaryl halides with arylboronic acids and styrene, respectively, using the microwave irradiation conditions. The electronic arrangement, type of hybridization, and nature of bonding in the Pd-complex were investigated by natural bond orbital analysis. Time-dependent density functional theory calculations were carried out to understand the electronic transitions in the related experimental observations. Graphical abstract: [Figure not available: see fulltext.]
- Darweesh, Ahmed F.,Mansour, Ahmed M.,Elwahy, Ahmed H. M.
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p. 1197 - 1205
(2016/07/30)
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- Palladium(II)-Schiff base complex immobilized covalently on h-BN: An efficient and recyclable catalyst for aqueous organic transformations
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A moisture- and air-stable palladium(II)-Schiff base complex supported on h-BN was simply prepared by using commercially available reagents. This nanomaterial was applied as an excellent and recyclable heterogeneous catalyst for the Suzuki and Heck cross-coupling reactions. And it has been characterized by FT-IR, XRD, SEM, XPS, TG and ICP-AES techniques. High yields, ligand-free, low reaction time, water as solvent, non-toxicity and recyclability of the catalyst are the main merits of these protocols. In addition, a series of pharmacologically relevant products were successfully synthesized using this catalyst. Above all, this work opens up an interesting and attractive avenue for the use of h-BN as an efficient support for heterogeneous catalysts.
- Li, Weijian,Lv, Guanghui,Cheng, Xu,Sang, Rui,Ma, Xiaojun,Zhang, Yong,Nie, Ruifang,Li, Jie,Guan, Mei,Wu, Yong
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supporting information
p. 8557 - 8564
(2016/12/07)
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- TRIAZOLOPYRIDINE COMPOUNDS AND METHODS FOR THE TREATMENT OF CYSTIC FIBROSIS
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The invention relates to a compound of Formula I or IA and methods of treating cystic fibrosis comprising the step of administering a therapeutically effective amount of a compound of Formula I or IA to a patient in need thereof:
- -
-
Paragraph 0159
(2016/05/02)
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- Palladium-Catalyzed Suzuki Reactions in Water with No Added Ligand: Effects of Reaction Scale, Temperature, pH of Aqueous Phase, and Substrate Structure
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The heterogeneous palladium-catalyzed Suzuki reactions between model aryl bromides (4-bromoanisole, 4-bromoaniline, 4-amino-2-bromopyridine, and 2-bromopyridine) and phenylboronic acid have been successfully conducted in water with no added ligand at the 100 mL scale using 20-40 mmol of aryl bromide. The product yields associated with these substrates were optimized, and key reaction parameters affecting the yields were identified. The results clearly indicate that the reaction parameters necessary to achieve high yields are substrate-dependent. In addition, it is demonstrated that aqueous Suzuki reactions of substrates containing basic nitrogen centers can produce quantitative yields of desired products in the absence of added ligand.
- Li, Zhao,Gelbaum, Carol,Heaner, William L.,Fisk, Jason,Jaganathan, Arvind,Holden, Bruce,Pollet, Pamela,Liotta, Charles L.
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p. 1489 - 1499
(2016/08/30)
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- Development of an air-stable, broadly applicable nickel source for nickel-catalyzed cross-coupling
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The synthesis of NiCl(o-tolyl)(TMEDA) (3; TMEDA = tetramethylethylenediamine) and its application in coupling reactions is described. In combination with a suitable ligand, precatalyst 3 was applied to a wide range of transformations, such as Suzuki, amination, Kumada, Negishi, Heck, borylation, and reductive coupling. Yields of products obtained with 3 are equal or superior to those obtained with common Ni sources such as Ni(cod)2 (1) and NiCl2(dme) (2). Importantly, and unlike 1, complex 3 is stable for months in air as a solid, which eliminates the need for a glovebox and greatly facilitates the reaction setup. Thus, complex 3 is the first highly versatile Ni source that combines the broad applicability of 1 with the air stability of 2.
- Magano, Javier,Monfette, Sebastien
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p. 3120 - 3123
(2015/05/20)
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- Structure-activity relationship study of E6 as a novel necroptosis inducer
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Necroptosis inducers represent a promising potential treatment for drug-resistant cancer. We herein describe the structure modification of E6, which was identified recently as a potent and selective necroptosis inducer. The studies described herein demonstrate for the first time that functionalized biphenyl derivatives possess necroptosis inducer activity. Furthermore, these studies have led to the identification of two promising compounds (5h and 5j) that can be used for further optimization studies as well as mechanism of action investigations.
- Mou, Jianfeng,Park, Ann,Cai, Yu,Yuan, Junying,Yuan, Chengye
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supporting information
p. 3057 - 3061
(2015/06/22)
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- Identification of two novel RET kinase inhibitors through MCR-based drug discovery: Design, synthesis and evaluation
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From an MCR fragment library, two novel chemical series have been developed as inhibitors of RET, which is a kinase involved in the pathology of medullary thyroid cancer (MTC). Structure activity relationship studies (SAR) identified two sub-micromolar tractable leads, 6g and 13g. 6g was confirmed to be a Type-II RET inhibitor. 13g and 6g inhibited RET in cells transformed by RET/C634. A RET DFG-out homology model was established and utilized to predict Type-II inhibitor binding modes.
- Frett, Brendan,Moccia, Marialuisa,Carlomagno, Francesca,Santoro, Massimo,Li, Hong-Yu
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p. 714 - 723
(2015/01/16)
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- Synthesis and characterization of hydrophilic theophylline base compounds and their use as ligands in the microwave assisted Suzuki-Miyaura couplings of halopyridines in water Dedicated to the memory of Prof. Dr. Armando Cabrera Ortiz pioneer of Catalysis in Mexico. Great Researcher but above all a Great Human Being
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Xanthine derivatives, caffeine (L1), theobromine (L2), theophylline (L3), 7-(β-hydroxyethyltheophylline) (L4), (7-(2,3-dihydroxypropyl)theophylline) (L5), and theophylline 7-acetic acid (L6) and the acetylated derivatives of the later three (L7-L9) were employed as ligands for the in situ palladium catalyzed Suzuki-Miyaura cross couplings of a series of halogenated pyridines. Optimized conditions were found where the diacetylated ligand (L8) was determined to be the best for this process, producing good to excellent yields in the couplings of halogenated anilines with phenylboronic acid under mild reaction conditions in water using microwave irradiation.
- Conelly-Espinosa, Patricia,Toscano, Ruben A.,Morales-Morales, David
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p. 5841 - 5845
(2015/01/09)
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- General suzuki coupling of heteroaryl bromides by using tri-tert-butylphosphine as a supporting ligand
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A general procedure for the fast Suzuki coupling of major families of heteroaryl bromides was realized by using Pd(OAc)2/PtBu3 as the catalyst. Many couplings were finished within minutes at room temperature in n-butanol. Different from previous studies, three typical heteroaryl bromides were systematically examined in couplings of various heteroaryl and aryl boronic acids. A fast, general coupling of heteroaryl bromides is realized by using a single palladium catalyst supported by tri-tert-butylphosphine.
- Zou, Yinjun,Yue, Guizhou,Xu, Jianwei,Zhou, Jianrong
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supporting information
p. 5901 - 5905
(2015/03/30)
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- METHOD OF SYNTHESIS MOLECULES USING CATALYST AND COMPOSITES THEREOF
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A method to synthesis molecules is provided. The method employs a catalyst for a cross- coupling react ion to obtain the molecule. The method comprises coupling boronic acid and halide in presence of the catalyst having graphite oxide supported palladium nanoparticles, a solvent and a base by heating. The heating is performed at a temperature lower than the temperature at which the graphite oxide deforms. The molecule is a biaryl. The method further provides obtaining complexs such as boscalid, telmisartan, valsartan, and SPPARMγ.
- -
-
Paragraph 0046; 0051; 0052
(2014/11/13)
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- SLC2A TRANSPORTER INHIBITORS
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Provided is a SLC2A class I transporter inhibitor compound for use in medicine, which compound comprises the following formula (I): wherein A and Z may be the same or different and are each independently selected from C, N, O and S; each X may be the same
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Page/Page column 157
(2014/12/12)
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- Palladium nanoparticles on graphite oxide: A recyclable catalyst for the synthesis of biaryl cores
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The synthesis of life saving drug molecules in a cost-effective and environmentally benign pathway is of paramount significance. We present an environment friendly protocol to prepare core moieties of top selling drug molecules such as boscalid and telmisartan using Suzuki-Miyaura coupling conditions. In contrast to the traditional synthesis of these pharmaceutically important molecules, we have accomplished a graphite oxide (GO) supported palladium nanoparticles (PdNPs) based catalyst which quantitatively produced these core biaryl moieties of top selling drug molecules in a recyclable way. The catalytic activity remained unchanged even after 16 successive catalytic cycles without incorporating any palladium metal impurity in the pharmaceutically significant organic products. A detailed study including IR spectroscopy, solid state NMR spectroscopy, X-ray photoelectron spectroscopy, and DFT calculation was employed to understand the role of solid support on the nondecaying recycling ability of the catalyst during the Suzuki-Miyaura coupling reaction. The study indicates a strong chemical interaction of the different functionalities present in the GO, with the palladium centers which is primarily responsible for such sustained catalytic activity during the consecutive Suzuki-Miyaura coupling cycles.
- Santra, Subhankar,Hota, Pradip Kumar,Bhattacharyya, Rangeet,Bera, Parthasarathi,Ghosh, Prasenjit,Mandal, Swadhin K.
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p. 2776 - 2789
(2014/01/06)
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- Synthesis of biaryls through a one-pot tandem borylation/Suzuki-Miyaura cross-coupling reaction catalyzed by a palladacycle
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The tricyclohexylphosphane adduct of cyclopalladated ferrocenylimine I exhibited high catalytic activity in the one-pot borylation/Suzuki-Miyaura coupling (BSC) reaction with low catalyst loading (2 mol-%). Various biaryls were obtained in good to excellent yields for 37 examples. This process was applied to aryl and heteroaryl halides (Br and Cl) containing a variety of functional groups and did not require an excess amount of phosphane ligand and the addition of the palladium catalyst in the second step. Cyclopalladated ferrocenylimine I exhibited high catalytic activity in the borylation/Suzuki- Miyaura coupling (BSC) reaction with low catalyst loading. Various unsymmetrical biaryls were obtained ingood to excellent yields in one pot. This protocol was applied to aryl and heteroaryl halides (Br and Cl) containing a variety of functional groups without adding catalyst in the second step. Copyright
- Wang, Lianhui,Cui, Xiuling,Li, Jingya,Wu, Yusheng,Zhu, Zhiwu,Wu, Yangjie
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p. 595 - 603
(2012/03/09)
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- A highly active catalytic system for Suzuki-Miyaura cross-coupling reactions of aryl and heteroaryl chlorides in water
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An easily available Pd(OAc)2/(2-mesitylindenyl) dicyclohexylphosphine/Me(octyl)3N+Cl-/K 3PO4·3H2O catalytic system was developed and it shows high catalytic activity in the Suzuki-Miyaura cross-coupling reaction of a diverse array of aryl and heteroaryl chlorides in water. Notably, this catalytic system also works with ultra-low loading of the catalyst with high turnover numbers.
- Mao, Shu-Lan,Sun, Yue,Yu, Guang-Ao,Zhao, Cui,Han, Zhi-Jun,Yuan, Jia,Zhu, Xiaolei,Yang, Qihua,Liu, Sheng-Hua
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p. 9410 - 9417
(2013/01/15)
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- Facile access to biaryls and 2-acetyl-5-arylbenzofurans via Suzuki coupling in water under thermal and microwave conditions
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The phosphine-free Suzuki-Miyaura carbon-carbon cross-coupling reactions of activated and deactivated aryl halides and 2-acetyl-5-bromobenzofuran with various aryl-or heteroarylboronic acids were investigated. A benzothiazole-based palladium(II) complex was used as a precatalyst for the reactions under both thermal and microwave conditions in air using water as a solvent. Georg Thieme Verlag Stuttgart - New York.
- Darweesh, Ahmed F.,Shaaban, Mohamed R.,Farag, Ahmad M.,Metz, Peter,Dawood, Kamal M.
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experimental part
p. 3163 - 3173
(2010/11/04)
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- A general and highly efficient method for the construction of aryl-substituted N-heteroarenes
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A general, simple and highly efficient method has been developed for the Pd(OAc)2-catalyzed ligand-free and aerobic Suzuki reaction of N-heteroaryl halides, which is strongly dependent on the molecular structure of solvent. A general, simple and highly efficient method has been developed for the Pd(OAc)2-catalyzed ligand-free and aerobic Suzuki reaction of N-heteroaryl halides including 2-pyridyl bromides, 3-pyridyl bromides, 3-quinolyl bromides, 5-pyrimidyl bromides and 2-pyrazyl chloride, which is strongly dependent on the molecular structure of solvent.
- Liu, Chun,Han, Na,Song, Xiaoxiao,Qiu, Jieshan
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supporting information; experimental part
p. 5548 - 5551
(2011/02/19)
-
- Synthesis and helicate formation of a new family of binol-based bis(bipyridine) ligands
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A new family of BINOL-based bis(bipyridine) ligands 1-3 (BINOL = 2,2 -dihydroxy-1,1 -binaphthyl) was prepared in enantiomerically pure form. Whereas the coordination of zinc(ll) ions to these ligands did not result in the selective formation of a specific metallosupramolecular aggregate,1 -3 were found to undergo highly diastereoselective self-assembly to D 2-symmetric dinuclear double-stranded helicates upon coordin ation to silver(l) and copper(l) ions and to D3-symmetric dinuclear triple-stranded helicates upon coordination to iron(ll) as demonstrated by mass spectrometry and by NMR and CD spectroscopy in combination with quantum chemical calculations.
- Bunzen, Jens,Bruhn, Torsten,Bringmann, Gerhard,Luetzen, Arne
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scheme or table
p. 3621 - 3630
(2009/08/14)
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- Surprising substituent effects on the self-assembly of helicates from bis(bipyridyl) BINOL ligands
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(Figure Presented) A number of different bis(bipyridyl) BINOL ligands were prepared using a convergent building block approach. These were studied with regard to their ability to undergo self-assembly to dinuclear helicates upon coordination to suitable late-transition-metal ions. Surprisingly, the substituents at the periphery of the ligand structure were found to have a marked influence on the outcome of the self-assembly processes with regard to the helicates composition, the stereoselectivity of the helicate formation, their redox reactivity, and their electronical properties as scrutinized by NMR- and CD-spectroscopic methods as well as ESI-mass spectrometric methods.
- Bunzen, Jens,Hovorka, Rainer,Luetzen, Arne
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supporting information; scheme or table
p. 5228 - 5236
(2009/12/04)
-
- NOVEL PIPERAZINE DERIVATIVES AS INHIBITORS OF STEAROYL-CoA DESATURASE
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The present invention relates to piperazine derivatives that act as inhibitors of stearoyl-CoA desaturase. The invention also relates to methods of preparing the compounds, compositions containing the compounds, and to methods of treatment using the compounds.
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Page/Page column 19; 20
(2009/10/01)
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- Structure-activity relationship study of EphB3 receptor tyrosine kinase inhibitors
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A structure-activity relationship study for a 2-chloroanilide derivative of pyrazolo[1,5-a]pyridine revealed that increased EphB3 kinase inhibitory activity could be accomplished by retaining the 2-chloroanilide and introducing a phenyl or small electron donating substituents to the 5-position of the pyrazolo[1,5-a]pyridine. In addition, replacement of the pyrazolo[1,5-a]pyridine with imidazo[1,2-a]pyridine was well tolerated and resulted in enhanced mouse liver microsome stability. The structure-activity relationship for EphB3 inhibition of both heterocyclic series was similar. Kinase inhibitory activity was also demonstrated for representative analogs in cell culture. An analog (32, LDN-211904) was also profiled for inhibitory activity against a panel of 288 kinases and found to be quite selective for tyrosine kinases. Overall, these studies provide useful molecular probes for examining the in vitro, cellular and potentially in vivo kinase-dependent function of EphB3 receptor.
- Qiao, Lixin,Choi, Sungwoon,Case, April,Gainer, Thomas G.,Seyb, Kathleen,Glicksman, Marcie A.,Lo, Donald C.,Stein, Ross L.,Cuny, Gregory D.
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supporting information; experimental part
p. 6122 - 6126
(2010/06/16)
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- A new class of pyrazolopyridine nucleus with fluorescent properties, obtained through either a radical or a Pd arylation pathway from N-azinylpyridinium N-aminides
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(Chemical Equation Presented) The synthesis of dipyridopyrazole and pyridopyrazolopyrazine derivatives - both of which incorporate a 3-aryl moiety - can be achieved in moderate yields by intramolecular radical arylation of pyridinium N-aminides using tris(trimethylsilyl)silane and azobisisobutyronitrile. Improved results were obtained on using Pd direct arylation in conjunction with microwave irradiation. A preliminary study into the fluorescent properties of the target compounds is also reported.
- Abet, Valentina,Nunez, Araceli,Mendicuti, Francisco,Burgos, Carolina,Alvarez-Builla, Julio
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scheme or table
p. 8800 - 8807
(2009/04/11)
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- Synthesis and mutagenic potency of structural isomers of 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine
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(Chemical Equation Presented) Synthesis of 2-amino-1-methyl-6- phenylimidazo[4,5-b]pyridine (PhIP), three structural isomers, and two desphenyl PhIP congeners has been carried out. Mutagenic potency was evaluated using S. typhimurium strain TA98 in the Ames test. Mutagenic potency increased in relation to structural features in these heterocyclic amines that allow extended resonance between the phenyl and imidazo[4,5-b]pyridine N2-amino substituents. By contrast, PhIP isomers, whose substitution disallows involvement of the phenyl group in their ammoimidazo resonance hybrids, and desphenyl congeners were from 86- to 234-fold less mutagenic than PhIP.
- Chrisman,Knize,Tanga
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experimental part
p. 1641 - 1649
(2009/08/09)
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- Kemp's triacid attached to octa-O-methyl resorc[4]arenes: conformations in solution and comparative binding studies with various 2-amino pyridines
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We synthesized the new supramolecular host molecules 7 and 13 based on functionalized resorcarenes bearing Kemp's triacid. Conformations in solution have been investigated and the influence of intra- and intermolecular hydrogen bonds from the triacid was
- Stoll, Ion,Mix, Andreas,Rozhenko, Alexander B.,Neumann, Beate,Stammler, Hans-Georg,Mattay, Jochen
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p. 3813 - 3825
(2008/09/20)
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- False positives in a reporter gene assay: Identification and synthesis of substituted N-pyridin-2-ylbenzamides as competitive inhibitors of firefly luciferase
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Luciferase reporter-gene assays are a commonly used technique in high-throughput screening campaigns. In this study, we report on a luciferase inhibitor (1), which emerged from an antagonistic G protein-coupled receptor luciferase reporter-gene assay scre
- Heitman, Laura H.,Van Veldhoven, Jacobus P. D.,Zweemer, Annelien M.,Ye, Kai,Brussee, Johannes,Ijzerrnan, Adriaan P.
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supporting information; experimental part
p. 4724 - 4729
(2009/06/18)
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- A nonacid degradable linker for solid-phase synthesis
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Synthesis and applications of two new nonacid degradable linkers as an alternative to the Wang linker for solid-phase synthesis are described. Resin from linker 2 looks superior to linker 1 in terms of yields for both anchoring of the first building block and cleavage and in terms of higher purity of the final product. Use of linker 2 avoids side reactions associated with the use of Wang resin due to an undesired cleavage during final acid treatment.
- Colombo, Aina,De La Figuera, Natalia,Fernandez, Joan Carles,Fernandez-Forner, Dolors,Albericio, Fernando,Forns, Pilar
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p. 4319 - 4322
(2008/03/11)
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- Direct synthesis of hetero-biaryl compounds containing an unprotected NH2 group via Suzuki-Miyaura reaction
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Hetero-biaryl compounds were prepared via the Suzuki-Miyaura coupling reaction of hetero-aryl moieties containing an unprotected NH2 group and arylboronic acids. D-t-BPF was found to be an efficient ligand for the cross-coupling of NH2/su
- Itoh, Takahiro,Mase, Toshiaki
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p. 3573 - 3577
(2007/10/03)
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- NITROGENOUS HETEROCYCLIC DERIVATIVE AND ORGANIC ELECTROLUMINESCENT ELEMENT EMPLOYING THE SAME
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A specific derivative of heterocyclic compound having nitrogen atom and an organic electroluminescence device comprising the compound. An organic electroluminescence device comprising at least one of organic compound layers including a light emitting layer sandwiched between an anode and a cathode, wherein said at least one of the organic compound layers comprises the derivative of the heterocyclic compound having nitrogen atom as a sole component or as mixed component. The organic electroluminescence device achieves elevation of luminance and excellent efficiency of light emission, and also achieves long lifetime by an improvement of an electrode adhesion.
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Page/Page column 87
(2008/06/13)
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- Total Syntheses of the Alkaloids Ipalbidinium and Clathryimine B
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The indolizidinium alkaloid ipalbidinium and the quinolizidinium alkaloid clathryimine B were prepared starting from brominated 2-aminopyridines using two Pd-catalyzed cross-coupling reactions and a Sandmeyer-type diazotation/iodination protocol as the key steps.
- Daab, Jochen C.,Bracher, Franz
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p. 573 - 583
(2007/10/03)
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- Efficient coupling of heteroaryl halides with arylboronic acids in the presence of a palladium-tetraphosphine catalyst
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Cis, cis, cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane: ·1/2[PdCl(C3H5)]2 system catalyses the Suzuki cross-coupling of heteroaryl halides with a range of arylboronic acids with very high ratio substrate/catalyst in good yields. Substrates such as pyridines, quinolines, thiophenes, an indole, pyrimidines or a furane have been used successfully.
- Feuerstein, Marie,Doucet, Henri,Santelli, Maurice
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p. 327 - 336
(2007/10/03)
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- Substituted 2-aminopyridines as inhibitors of nitric oxide synthase
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Substituted 2-aminopyridine compounds of Formula (I) and pharmaceutically acceptable salts which have been found useful in the treatment of nitric oxide synthase mediated diseases and disorders. STR1
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- Reaction of Organoboron Compounds with Organic Halides in Aqueous Media, Catalyzed by "Ligand-Free" Palladium
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The results of investigations of the reactions between aryllboric acids or sodium tetraphenylborate and organic halides in water and DMF- and acetone-water mixtures, catalyzed by palladium salts containing no phosphine ligands [Pd(OAc)2, PdCl2], are considered.
- Bumagin,Bykov
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p. 1925 - 1938
(2007/10/03)
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- PALLADIUM-CATALYZED CROSS-COUPLING OF PHENYLBORONIC ACID WITH HETEROCYCLIC AROMATIC HALIDES
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The coupling reaction of bromo- and iodopyridines 1 with phenylboronic acid (2a) by Pd(Ph3P)4 provides a convenient route to phenylpyridines, even when electrodonating or - withdrawing substituents are present.The method is also successful for the preparation of other phenylated N-containing heterocycles 5 as phenylquinolines and -pyridines.
- Stavenuiter, Johannes,Hamzink, Martin,Hulst, Rob van der,Zomer, Gijsbert,Westra, Gerard,Kriek, Erik
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p. 2711 - 2716
(2007/10/02)
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- THE SYNTHESIS OF THE COOKED-BEEF MUTAGEN 2-AMINO-1-METHYL-6-PHENYLIMIDAZOPYRIDINE AND ITS 3-METHYL ISOMER
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2-Amino-1-methyl-6-phenylimidazopyridine, a mutagenic compound newly isolated from cooked beef, and its 3-methyl isomer have been synthesized.The spectroscopic data and the mutagenicity of the isomers are compared.
- Knize, Mark G.,Felton, James S.
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p. 1815 - 1819
(2007/10/02)
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- 1-Benzoyl-3-(arylphyridyl)urea compounds
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The present invention is directed to 1-benzoyl-3-(arylpyridyl)urea compounds useful as insecticides.
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- Chichibabin reaction
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In a Chichibabin amination of a pyridine base by sodamide in an organic solvent, the improvement comprising conducting the reaction under pressure of at least about 50 psi in the gas phase above the reaction mixture and adding ammonia to the mixture sufficient to produce a partial pressure of ammonia of at least about 5 psi in the gas phase. Preferred temperature and pressure ranges are disclosed, as are catalysts and other preferred steps for practicing the reaction. Significant results are obtained including improved and changed yields from those classically expected in Chichibabin aminations, including new compositions of matter in at least one case.
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- 3-TETRAZOLO-5,6,7,8-SUBSTITUTED PYRIDO[1,2-a]PYRIMIDIN-4-ONES
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A novel series of optionally substituted 3-(1H-tetrazol-5-yl)-4H-pyrido[1,2-a]pyrimidin-4-ones is provided for use as inhibitors of allergic reactions. The compounds exhibit antiallergy activity by both oral and parenteral routes of administration
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