- Coupling ofN-tosylhydrazones with tetrazoles: synthesis of 2-β-d-glycopyranosylmethyl-5-substituted-2H-tetrazole type glycomimetics
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Coupling reactions ofO-peracylated 2,6-anhydro-aldose tosylhydrazones (C-(β-d-glycopyranosyl)formaldehyde tosylhydrazones) with tetrazoles were studied under metal-free conditions using thermic or microwave activation in the presence of different bases. The reactions proved highly regioselective and gave the corresponding, up-to-now unknown 2-β-d-glycopyranosylmethyl-2H-tetrazoles in 7-67% yields. The method can be applied to get new types of disaccharide mimetics, 5-glycosyl-2-glycopyranosylmethyl-2H-tetrazoles, as well. Galectin binding studies withC-(β-d-galactopyranosyl)formaldehyde tosylhydrazone and 2-(β-d-galactopyranosylmethyl)-5-phenyl-2H-tetrazole revealed no significant inhibition of any of these lectins.
- Kaszás, Tímea,Cservenyák, Ivett,Juhász-Tóth, éva,Kulcsár, Andrea E.,Granatino, Paola,Nilsson, Ulf J.,Somsák, László,Tóth, Marietta
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supporting information
p. 605 - 618
(2021/02/06)
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- Copper-based catalysts derived from salen-type ligands: Synthesis of 5-substituted-1: H-tetrazoles via [3+2] cycloaddition and propargylamines via A3-coupling reactions
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Base-metal copper(ii) complexes derived from unsymmetrical salen-type ligands were designed and synthesized using ligands L1H to L4H in moderate yield. The synthesized unsymmetrical ligands L1H to L4H and the corresponding copper complexes (1-4) were characterized by UV-visible, IR and ESI-MS spectroscopic studies. Molecular structures of complexes 1, 2 and 4 were determined by X-ray crystallography. Copper complexes 1-4 were employed as catalysts for [3+2] cycloaddition and A3-coupling reactions. The mutual approach of salen-type ligands and metals via active participation of ligands allow to achieve the catalytic reactions. Reaction pathways were proposed and possible intermediate species during the catalytic cycle were successfully characterized by ESI-MS spectroscopic studies. This journal is
- Singh, Anshu,Maji, Ankur,Mohanty, Aurobinda,Ghosh, Kaushik
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p. 18399 - 18418
(2020/11/13)
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- TMSN3-Bu2Sn(OAc)2: A modified and mild reagent system for Wittenberger tetrazole-synthesis
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Treatments of various nitriles with TMSN3 and Bu2Sn(OAc)2 at 30 °C in benzene for 60 h yielded the corresponding 5-substituted 1H-tetrazoles in good to excellent yields. This method is a mild and efficient alternative reagent system for Wittenberger tetrazole-synthesis that uses TMSN3 and Bu2SnO in toluene at high temperature (93–110 °C) for 24–72 h.
- Yoneyama, Hiroki,Oka, Naoki,Usami, Yoshihide,Harusawa, Shinya
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- NOVEL ARYL OR HETEROARYL TRIAZOLONE DERIVATIVES OR SALTS THEREOF, OR PHARMACEUTICAL COMPOSITIONS COMPRISING THE SAME
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The present technology provides aryl or heteroaryl triazolone derivatives or pharmaceutically acceptable salts thereof, preparation processes thereof, pharmaceutical compositions comprising the same, and the use thereof. The aryl or heteroaryl triazolone derivatives or their pharmaceutically acceptable salts exhibit selective inhibitory activity on VAP-1 and therefore can be usefully applied, e.g., for the treatment and prophylaxis of nonalcoholic hepatosteatosis (NASH).
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Paragraph 0368-0370
(2019/10/15)
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- Cationic organotin cluster [t-Bu2Sn(OH)(H2O)]2 2+2OTf?-catalyzed one-pot three-component syntheses of 5-substituted 1H-tetrazoles and 2,4,6-triarylpyridines in water
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The cationic organotin cluster [t-Bu2Sn(OH)(H2O)]2 2+2OTf? is easy to prepare and stable in air. The catalytic activity of [t-Bu2Sn(OH)(H2O)]2 2+2OTf? as a neutral organotin Lewis acid catalyst is probed through the one-pot three-component syntheses of 5-substituted 1H-tetrazoles from aldehydes, hydroxylamine hydrochloride and sodium azide, and of 2,4,6-triarylpyridines from aromatic aldehydes, substituted acetophenones and ammonium acetate. The reactions proceed well in the presence of 1?mol% of [t-Bu2Sn(OH)(H2O)]2 2+2OTf? in water and provide the corresponding 5-substituted 1H-tetrazoles and 2,4,6-triarylpyridines in good to excellent yields. The method reported has several advantages such as the catalyst being neutral, low catalyst loading and use of water as a green solvent.
- Wang, Hongshe,Zhao, Weixing,Du, Juan,Wei, Fenyan,Chen, Qi,Wang, Xiaomei
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- Humic acid as an efficient and reusable catalyst for one pot three-component green synthesis of 5-substituted 1: H -tetrazoles in water
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Humic acid is a non toxic, inexpensive, easily available high-molecular weight polymer. A simple and facile one pot three-component synthesis of 5-substituted 1H-tetrazoles from aldehydes, hydroxyamine hydrochloride and sodium azide using humic acid as an efficient catalyst in water is described. The method reported has several advantages such as high to excellent yields, easy work-up, mild reaction conditions, use of water as a green solvent, and a commercially available, nontoxic and reusable catalyst.
- Wang, Hongshe,Wang, Yichun,Han, Yinfeng,Zhao, Weixing,Wang, Xiaomei
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p. 784 - 789
(2020/01/23)
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- Copper(II)-faciliated synthesis of substituted thioethers and 5-substituted 1H-tetrazoles: Experimental and theoretical studies
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Benzoylhydrazine based Schiff base-ligated two new copper(II) complexes, [Cu(L1)2] (1) and [Cu(L2)2] (2) were synthesized by the reaction of Cu(CH3COO)2·H2O with respective Schiff base ligand 1-[(4-nitrophenyl)ethylidene] benzohydrazide (HL1) or 1-[(4-methoxyphenyl)ethylidene] benzohydrazide (HL2). Both complexes were isolated as greenish solid and fully characterized by elemental analysis, FT-IR, EPR, thermo-gravimetric (TG) analysis and Cyclic Voltammetry. The molecular structures of both complexes have also been determined by single crystal X-ray crystallography, which confirmed the coordination of Schiff base ligands through N, O donor atoms and distorted square planar geometry around the Cu(II) ion. Both complexes were found to be good homogeneous catalysts for the synthesis of a wide range of substituted thioethers and 5-substituted 1H-tetrazoles in 92% and 93% yield, respectively, at a low catalyst loading (0.5 mol%). The bond angles and distances, as discerned from the DFT calculations, commusurated with the experimental findings. The energy difference between the HOMO and the LUMO, calculated from DFT studies, was found to be 5.645 eV and 6.459 eV for complex 1 and complex 2, respectively. These results are in harmony with the observed higher catalytic activity of complex 1.
- Layek, Samaresh,Agrahari, Bhumika,Dey, Shuvankar,Ganguly, Rakesh,Pathak, Devendra D.
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p. 194 - 206
(2019/06/24)
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- Synthesis of tetrazoles, triazoles, and imidazolines catalyzed by magnetic silica spheres grafted acid
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The magnetically separable catalysts are used in the synthesis of N-containing heterocycles, including tetrazoles, triazoles, and imidazolines. The magnetic silica sphere grafted sulfonic acid (MSS-SO3H) is suitable for the synthesis of 1,2,3-triazole via the cycloaddition of nitroalkene with NaN3, whereas the zinc-modified silica sphere catalyst (MSS-SO3Zn) is more suitable for the synthesis of tetrazoles. The MSS-SO3Zn catalyst also works well for the synthesis of 2-substituted imidazoline via the condensation of nitriles with ethylenediamine. Both of the MSS-SO3H and MSS-SO3Zn catalysts can be recovered easily by a magnet, and they can be reused without further tedious activation.
- Jiang, Ruihang,Sun, Hong-Bin,Li, Shuang,Zhan, Kun,Zhou, Junjie,Liu, Lei,Zhang, Kai,Liang, Qionglin,Chen, Zhangpei
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supporting information
p. 2652 - 2662
(2018/11/26)
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- Unprecedented formation of a μ-oxobridged polymeric copper(II) complex: Evaluation of catalytic activity in synthesis of 5-substituted 1H-tetrazoles
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The reaction of CuCl2·2H2O with Schiff base ligand, 4-[(2-hydroxy-3-methoxybenzylidene)amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3-one] (hmdpH), in 1:1 molar ratio led to a novel and unprecedented oxo-bridged polymeric copper (II) complex, [Cu(μ-O) (hmdp)]n. The complex was isolated as crystalline solid and characterized by FTIR, UV–visible and EPR spectroscopic techniques. The molecular structure of the complex was also determined by single crystal X-ray diffraction studies. The formation of the complex is unique and unprecedented in the sense that one of the CH3 group of the 4-aminoantipyrene unit of the Schiff base ligand is oxidized in situ to CH2OH, during the complex formation. The catalytic potential of the complex has been demonstrated in the synthesis of a series of 5-substituted 1H-tetrazoles via [3 + 2]-cycloaddition reactions of substituted benzonitriles and sodium azide in ethylene glycol.
- Layek, Samaresh,Ganguly, Rakesh,Pathak, Devendra D.
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- Engineering a Cu-MOF Nano-Catalyst by using Post-Synthetic Modification for the Preparation of 5-Substituted 1H-Tetrazoles
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A new nano scale Cu-MOF has been obtained via post-synthetic metalation by immersing a Zn-MOF as a template in DMF solutions of copper(II) salts. The Cu-MOF serves as recyclable nano-catalyst for the preparation of 5-substituted 1H-tetrazoles via [3?+?2] cycloaddition reaction of various nitriles and sodium azide in a green medium (PEG). The post-synthetic metalated MOF were characterized by FT-IR spectroscopy, powder X-ray diffraction (PXRD), atomic absorption spectroscopy (AAS), and energy dispersive X-ray spectroscopy (EDX) techniques. The morphology and size of the nano-catalyst were determined by field emission scanning electron microscopy (FE-SEM).
- Salahshournia, Behrang,Hamadi, Hosein,Nobakht, Valiollah
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- A focused fragment library targeting the antibiotic resistance enzyme - Oxacillinase-48: Synthesis, structural evaluation and inhibitor design
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β-Lactam antibiotics are of utmost importance when treating bacterial infections in the medical community. However, currently their utility is threatened by the emergence and spread of β-lactam resistance. The most prevalent resistance mechanism to β-lactam antibiotics is expression of β-lactamase enzymes. One way to overcome resistance caused by β-lactamases, is the development of β-lactamase inhibitors and today several β-lactamase inhibitors e.g. avibactam, are approved in the clinic. Our focus is the oxacillinase-48 (OXA-48), an enzyme reported to spread rapidly across the world and commonly identified in Escherichia coli and Klebsiella pneumoniae. To guide inhibitor design, we used diversely substituted 3-aryl and 3-heteroaryl benzoic acids to probe the active site of OXA-48 for useful enzyme-inhibitor interactions. In the presented study, a focused fragment library containing 49 3-substituted benzoic acid derivatives were synthesised and biochemically characterized. Based on crystallographic data from 33 fragment-enzyme complexes, the fragments could be classified into R1 or R2 binders by their overall binding conformation in relation to the binding of the R1 and R2 side groups of imipenem. Moreover, binding interactions attractive for future inhibitor design were found and their usefulness explored by the rational design and evaluation of merged inhibitors from orthogonally binding fragments. The best inhibitors among the resulting 3,5-disubstituted benzoic acids showed inhibitory potential in the low micromolar range (IC50 = 2.9 μM). For these inhibitors, the complex X-ray structures revealed non-covalent binding to Arg250, Arg214 and Tyr211 in the active site and the interactions observed with the mono-substituted fragments were also identified in the merged structures.
- Akhter, Sundus,Lund, Bjarte Aarmo,Ismael, Aya,Langer, Manuel,Isaksson, Johan,Christopeit, Tony,Leiros, Hanna-Kirsti S.,Bayer, Annette
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supporting information
p. 634 - 648
(2018/01/19)
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- Synthesis and crystal structures of salen-type Cu(II) and Ni(II) Schiff base complexes: application in [3+2]-cycloaddition and A3-coupling reactions
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The synthesis of two new salen-type Schiff base complexes of the type [Cu(L)]·0.5H2O, 1, and [Ni(L)], 2, from the reaction of a 6,6′-[(1E,1′E)-(cyclohexane-1,2-diylbis(azanylylidene))bis(methanylylidene)bis(3-(diethylamino)phenol)] salen-type Schiff base ligand (H2L) with Cu(OAc)2·H2O and Ni(OAc)2·4H2O in methanol at room temperature, respectively, is described. The complexes are isolated as coloured crystalline solids and characterized by elemental analysis, FT-IR spectroscopy, UV-visible spectroscopy and single crystal X-ray diffraction studies. The paramagnetic nature of complex 1, having giso = 2.076, was confirmed by EPR studies, which indicated a distorted square planar geometry of the complex. In contrast to this, the nickel complex was found to be diamagnetic in nature and it was additionally characterized by 1H NMR. The crystal structures of complexes 1 and 2 confirm the distorted square planar geometry of both the complexes. Complex 1 was found to be a better catalyst for the synthesis of a series of 5-substituted 1H-tetrazoles from nitriles and sodium azide via [3+2]-cycloaddition and for the A3-coupling reaction of aldehydes, secondary amines and terminal alkynes with a low catalyst loading (0.7 and 0.9 mol%, respectively) as compared to complex 2. Complex 1 is novel in the sense that, being a homogeneous catalyst, it can be recovered almost quantitatively in both reactions and recycled up to four times to afford good yields of the corresponding products.
- Agrahari, Bhumika,Layek, Samaresh,Ganguly, Rakesh,Pathak, Devendra D.
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p. 13754 - 13762
(2018/08/21)
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- Cu(NO3)2-catalysed direct synthesis of 5-substituted 1H-tetrazoles from alcohols or aldehydes
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A simple, convenient and practical protocol to synthesise 5-substituted 1H-tetrazoles from alcohols or aldehydes is reported. Using ammonia and sodium azide as nitrogen sources and Cu(NO3)2 as catalyst, benzylic alcohols and benzaldehydes were directly converted into 5-substituted 1H-tetrazoles in a one-pot procedure.
- Tao, Chuanzhou,Wang, Bin,Sun, Lei,Yi, Jiuyin,Shi, Dahua,Wang, Jian,Liu, Weiwei
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- Triple reuptake inhibitors: Design, synthesis and structure–activity relationship of benzylpiperidine–tetrazoles
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Monoamine transporters are important targets in the treatment of various central nervous disorders. Several limitations of traditional reuptake inhibitors, like delayed onset of action, insomnia, and sexual dysfunction, have compelled the search for safer, more effective compounds. In this study, we have sought to identify novel monoamine reuptake inhibitors. Based upon the docking study of compounds that we had reported previously, aromatic rings (A1) were modified to generate a novel series of benzylpiperidine–tetrazoles. Thirty-one compounds were synthesized and evaluated for their triple reuptake inhibition of serotonin, norepinephrine and dopamine. Triple reuptake inhibitor, compound 2q, in particular, showed potent serotonin reuptake inhibition, validating our design approach.
- Paudel, Suresh,Min, Xiao,Acharya, Srijan,Khadka, Daulat Bikram,Yoon, Goo,Kim, Kyeong-Man,Cheon, Seung Hoon
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p. 5278 - 5289
(2017/10/06)
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- A 1, 2, 4-oxadiazole micromolecule the main body material and its preparation method, application
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The invention discloses a 1, 2, 4-oxadiazole micromolecule main body material. The 1, 2, 4-oxadiazole micromolecule main body material contains one or multiple electrophilic 1, 2, 4-oxadiazoles which serve as electron acceptor units, wherein the tail ends of molecules are connected to electron donor units. The invention also discloses a preparation method of the micromolecule main body material. The preparation method is characterized in that a dibromo substituted intermediate, namely a 1, 2, 4-oxadiazole compound is prepared by using bromobenzonitrile as a reaction raw material, and then electron donor units are connected to the dibromo substituted intermediate, namely the 1, 2, 4-oxadiazole compound through Suzuki coupling reaction. The invention also discloses an application of the 1, 2, 4-oxadiazole micromolecule main body material. The 1, 2, 4-oxadiazole micromolecule main body material has relatively good solubility and film-forming property, relatively strong eletrophilicity, relatively low LUMO (Lowest Unoccupied Molecular Orbital) energy level and relatively high electronic mobility.
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Paragraph 0096 - 0098
(2017/02/24)
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- Double-ring substituted pyrazolone azo derivatives, their preparation and use (by machine translation)
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The invention belongs to the field of pharmaceutical chemicals, relates to a twin-ring substituted pyrazolone azo derivatives, preparation method thereof, its pharmaceutical composition and use thereof. In particular, the present invention is shown in formula I compound or its pharmaceutically acceptable salt or solvate. The invention relates also to the preparation method of the compound I, which comprises a pharmaceutical composition and their pharmaceutical use. The invention of the formula I compounds are effective TPO agonist, is good medicine for treating thrombocytopenia. Type I. (by machine translation)
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Paragraph 0240; 0242; 0243; 0244
(2017/01/02)
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- Efficient synthesis of 5-substituted 1H-tetrazoles catalysed by silver(I) bis(trifluoromethanesulfoyl)nimide
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An efficient method is developed for the synthesis of 5-substituted 1H-tetrazoles through the [3 + 2] cycloaddition reaction of nitriles with sodium azide using silver(I) bis(trifluoromethanesulfonyl)imide (AgNTf2) as a catalyst. This procedure provides mild reaction conditions, short reaction times and high yields.
- Wang, Hongshe,Zhao, Weixing
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p. 321 - 323
(2015/08/11)
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- Multi-component one-pot reaction of aldehyde, hydroxylamine and sodium azide catalyzed by Cu-MCM-41 nanoparticles: A novel method for the synthesis of 5-substituted 1H-tetrazole derivatives
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A simple and efficient procedure for the synthesis of 5-substituted 1H-tetrazole derivatives has been developed using a one-pot, three-component reaction of various aldehydes, hydroxylamine and sodium azide in the presence of a catalytic amount of Cu-MCM-41, as a nanostructured, heterogeneous and reusable catalyst. In this research, Cu-MCM-41 nanoparticles with three Cu/Si molar ratios were prepared and characterized using various techniques. The characterization and optimization results show that the catalyst with a Cu/Si molar ratio of 0.050 has the best catalytic activity.
- Abdollahi-Alibeik, Mohammad,Moaddeli, Ali
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p. 2116 - 2122
(2015/03/18)
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- Design and synthesis of novel anthracene derivatives as n-type emitters for electroluminescent devices: A combined experimental and DFT study
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Six novel anthracene-oxadiazole derivatives, 4a (2-(4-(anthracen-9-yl) phenyl)-5-p-tolyl-1,3,4-oxadiazole), 4b (2-(4-(anthracen-9-yl)phenyl)-5-(4-tert- butylphenyl)-1,3,4-oxadiazole), 4c (2-(4-(anthracen-9-yl)phenyl)-5-(4- methoxyphenyl)-1,3,4-oxadiazole), 8a (2-(4-(anthracen-9-yl)phenyl)-5-m-tolyl-1, 3,4-oxadiazole), 8b (2-(3-(anthracen-9-yl)phenyl)-5-(4-tert-butylphenyl)-1,3,4- oxadiazole) and 8c (2-(3-(anthracen-9-yl)phenyl)-5-(3,4,5-trimethoxyphenyl)-1,3, 4-oxadiazole) have been synthesized and characterized for use as emitters in organic light emitting devices (OLEDs). They show good thermal stability (T d, 297-364 °C) and glass transition temperatures (Tg) in the range of 82-98 °C, as seen from the thermo gravimetric analysis and differential scanning calorimetric studies. The solvatochromism phenomenon and electrochemical properties have been studied in detail using UV-Vis absorption, fluorescence spectroscopy and cyclic voltammetry. TD-DFT calculations have been carried out to understand the electrochemical and photophysical properties. The spatial structures of 4b and 8c are further confirmed by X-ray diffraction analysis. Un-optimized non-doped electroluminescent devices were fabricated using these anthracene derivatives as emitters with the following device configuration: ITO (120 nm)/α-NPD (30 nm)/4a-4c or 8a-8c (35 nm)/BCP (6 nm)/Alq3 (28 nm)/LiF (1 nm)/Al (150 nm). Among all the six compounds, 8a displays the maximum brightness of 1728 cd m-2 and current efficiency 0.89 cd A-1. Furthermore, as an electron transporter, 8a exhibited superior performance (current efficiency is 11.7 cd A-1) than the device using standard Alq3 (current efficiency is 8.69 cd A-1), demonstrating its high potential for employment in OLEDs. These results indicate that the new anthracene-oxadiazole derivatives could play an important role in the development of OLEDs. The Royal Society of Chemistry and Owner Societies.
- Mallesham,Balaiah,Reddy, M. Ananth,Sridhar,Singh, Punita,Srivastava, Ritu,Bhanuprakash,Rao, V. Jayathirtha
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p. 342 - 357
(2014/02/14)
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- Nano TiO2/SO42- as a heterogeneous solid acid catalyst for the synthesis of 5-substited-1 H-tetrazoles
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An efficient and economical protocol for the synthesis of 5-substituted-1H-tetrazoles from various nitriles and sodium azide is reported using nano TiO2/SO42+ as an effective heterogeneous catalyst.A wide variety of aryl nitriles underwent [3 + 2] cycloaddition to afford tetrazoles in good to excellent yields.
- Hosseini-Sarvari, Mona,Najafvand-Derikvandi, Sepideh
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p. 1007 - 1012
(2015/01/09)
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- Organocatalysis by an aprotic imidazolium zwitterion: A dramatic anion-cation cooperative effect on azide-nitrile cycloaddition
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An aprotic imidazole based zwitterionic-salt, 4-(3-methylimidazolium)butane sulfonate (MBS) has been found to be an efficient organocatalyst for the synthesis of 5-substituted 1H-tetrazoles by the cycloaddition of aryl nitriles with NaN3 under solvent-free conditions. Both the cation and the anion cooperatively affect the reaction and the C2-H of the imidazolium moiety plays a crucial role in "electrophilic activation" of the nitrile through hydrogen bond formation.
- Rahman, Matiur,Roy, Anupam,Ghosh, Monoranjan,Mitra, Shubhanjan,Majee, Adinath,Hajra, Alakananda
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p. 6116 - 6119
(2014/01/23)
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- Facile synthesis of 5-substituted-1H-tetrazoles and 1-substituted-1H- tetrazoles catalyzed by recyclable 4′-phenyl-2,2′:6′,2″- terpyridine copper(II) complex immobilized onto activated multi-walled carbon nanotubes
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5-Substituted-1H-tetrazoles can conveniently be synthesized from the corresponding nitriles by reaction with NaN3 using the efficient and recyclable heterogeneous catalyst prepared by immobilization of copper(II) complex of 4′-phenyl-2,2′:6′,2″-terpyridine on activated multi-walled carbon nanotubes [AMWCNTs-O-Cu(II)-PhTPY]. Excellent results were obtained in each case affording the corresponding tetrazole adducts in good to excellent yields. In general, aromatic nitriles with electron-donating group could be accomplished as well as that with electron-withdrawing groups. By leaving out nitrile from the reaction and adding CH(OEt)3 and amines bearing various substituents, 1-substituted-1H-tetrazoles formed in water in high yields. The reported protocols have the advantages of rapid assembly of a host of heterocyclic systems in high yields with the added advantage of recycling and reuse of the catalyst.
- Sharghi, Hashem,Ebrahimpourmoghaddam, Sakineh,Doroodmand, Mohammad Mahdi
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- Highly efficient synthesis of 1- and 5-substituted 1H-tetrazoles using chitosan derived magnetic ionic liquid as a recyclable biopolymer-supported catalyst
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A general method for the efficient synthesis of 1- and 5-substituted 1H-tetrazoles from nitriles and amines is described using chitosan supported magnetic ionic liquid nanoparticles (CSMIL) as a novel heterogeneous catalyst. The application of this catalyst allows the synthesis of a variety of tetrazoles in high yields at low temperature. This new magnetic catalyst has been prepared from chitosan (the most abundant biopolymer in nature and cheap industrial waste) and methyl imidazole (a widely available backbone of ionic liquids) which was reacted with FeCl3 to obtain the CS-EMImFeCl4 catalyst. This methodology illustrates a very simple procedure, with wide applicability, environmental friendliness and reusability of catalyst. The new catalyst was characterized using some different microscopic and spectroscopic techniques such as transmission electron microscopy (TEM), scanning electron microscopy (SEM), FTIR spectroscopy, and Raman spectroscopy. The novel catalyst has therefore a great potential to be used in green processes. The Royal Society of Chemistry 2013.
- Khalafi-Nezhad, Ali,Mohammadi, Somayeh
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p. 4362 - 4371
(2013/05/08)
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- Synthesis and physical properties of meta-terphenyloxadiazole derivatives and their application as electron transporting materials for blue phosphorescent and fluorescent devices
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Two m-terphenyloxadiazole-based electron transporting materials, bis(2-tert-butyl-1,3,4-oxadiazole-5-diyl)-3,3′-m-terphenyl (tOXD-mTP) and bis(2-(4-tert-butylphenyl)-1,3,4-oxadiazole-5-diyl)-3,3′-m-terphenyl (tpOXD-mTP) were synthesized and characterized. These two molecules contained two oxadiazolyl groups and a m-terphenyl linkage as the core structure achieving high triplet energy gaps (ET) of 2.83 and 2.90 eV, respectively. The application of tOXD-mTP and tpOXD-mTP as the electron transporting materials (ETM) in bis(4′,6′-difluorophenylpyridinato)-iridium(iii) picolinate (FIrpic)-based blue phosphorescent light-emitting devices effectively confines the triplet exciton in the emitting layers. One of the electroluminescent (EL) devices using FIrpic as the dopant showed an excellent current efficiency of 43.3 cd A-1 and an external quantum efficiency (EQE) of 23.0% with CIE (Commission International de l'Eclairage) coordinates of (0.13, 0.29). The bis(4′,6′-difluorophenylpyridinato)-iridium(iii) tetra(1-pyrazolyl)borate (FIr6)-based deeper blue EL device exhibited a high current efficiency of 42.5 cd A-1 and external quantum efficiency of 25.0% with CIE coordinates of (0.14, 0.23). These two tOXD-mTP and tpOXD-mTP based devices show device efficiencies two to three times higher than that based on the well-known electron transporting material 1,3-bis[(4-tertbutylphenyl)-1, 3,4-oxadiazolyl]phenylene (OXD-7).
- Wu, Cheng-An,Chou, Ho-Hsiu,Shih, Cheng-Hung,Wu, Fang-Iy,Cheng, Chien-Hong,Huang, Heh-Lung,Chao, Teng-Chih,Tseng, Mei-Rurng
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scheme or table
p. 17792 - 17799
(2012/09/22)
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- Phosphomolybdic acid (H3Mo12O40P) as a reusable heterogeneous catalyst for the synthesis of 5-substituted 1 H-Tetrazoles via [2+3] cycloaddition of nitriles and sodium azide
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An efficient and practical protocol for the preparation of 5-substituted 1H-tetrazole derivatives is reported using phosphomolybdic acid as an effective heterogeneous catalyst. Good yields, simple methodology, and easy workup make this protocol more attractive for the diversity-oriented synthesis of these heterocycle libraries. The catalyst can be recycled three times with good yields.
- Takale, Santosh,Manave, Smita,Phatangare, Kiran,Padalkar, Vikas,Darvatkar, Nitin,Chaskar, Atul
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experimental part
p. 2375 - 2381
(2012/06/29)
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- CuFe2O4 nanoparticles: A magnetically recoverable and reusable catalyst for the synthesis of 5-substituted 1H-tetrazoles
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An efficient and economical protocol for the synthesis of 5-substituted 1H-tetrazoles from various nitriles and sodium azide is described using magnetically recoverable and reusable CuFe2O4 nanoparticles. A wide variety of aryl nitriles underwent [2+3] cycloaddition under mild reaction conditions to afford tetrazoles in good to excellent yields. The catalyst was magnetically separated and reused five times without significant loss of catalytic activity.
- Sreedhar,Kumar, A. Suresh,Yada, Divya
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experimental part
p. 3565 - 3569
(2011/07/29)
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- Aluminum(III) hydrogensulfate: An efficient solid acid catalyst for the preparation of 5-substituted 1H-tetrazoles
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An efficient method for preparation of 5-substituted 1H-tetrazoles via [2+3] cycloaddition of nitriles and sodium azide is reported using aluminum(III) hydrogensulfate as an effective solid acid. This method has the advantages of good yields, simple methodology, and easy workup. Copyright
- Sajadi, S. Mohammad,Khalaj, Mehdi,Jamkarani, Sayyed Mohammad Hosseini,Maham, Mehdi,Kashefib, Mehrdad
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scheme or table
p. 3053 - 3059
(2011/09/12)
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- Tetrazoles: LVI. Synthesis of 5-substituted tetrazoles under microwave activation in the presence of heterogeneous catalyst (Zinc oxide)
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Reactions of aromatic and heteroaromatic nitriles with sodium azide in the presence of zinc oxide under the conditions of microwave activation provide 5-aryl(hetaryl)tetrazoles in high yields. Pleiades Publishing, Ltd., 2011.
- Myznikov,Efimova, Yu. A.,Artamonova,Koldobskii
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experimental part
p. 728 - 730
(2011/08/06)
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- Montmorillonite K-10 clay as an efficient reusable heterogeneous catalyst for the solvent-free microwave mediated synthesis of 5-substituted 1H-tetrazoles
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Various 5-substituted 1H-tetrazole derivatives were synthesized in a simple and environmentally benign method from the reaction of aryl and benzyl nitriles with sodium azide in solvent-free media using montmorillonite K-10 clay as solid recyclable heterogeneous acidic catalyst and microwave irradiation in good yields and short reaction times. Copyright
- Marvi, Omid,Alizadeh, Abdolhamid,Zarrabi, Saeid
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experimental part
p. 4001 - 4004
(2012/04/10)
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- Synthesis and characterization of a new series of blue fluorescent 2, 6-linked 9, 10-diphenylanthrylenephenylene copolymers and their application for polymer light-emitting diodes
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A series of new 9, 10-diphenylanthracene-based, 2, 6-linked blue-light-emitting copolymers bearing hole- or electron-transporter as well as bulky substituent were successfully synthesized. Photophysical, thermal, electrochemical, and electroluminescence (EL) properties of these copolymers were studied and characterized. Bright and efficient blue fluorescence in the solid state was achieved by incorporating bulky substituent into the copolymer backbone. Both hole- and electron-transport-substituted copolymers apparently enhanced the electroluminescent performance of their polymeric light-emitting diodes (PLEDs). A diphenylvinyl-bearing copolymer (pDPV) PLED exhibited sky-blue EL (λETmax=473 nm, CIEx,y=0.16,0.28) with peak luminous efficiency of 2.21 cd/A; a N-carbazole bearing copolymer (pCBZ) PLED displayed a blue EL (λELmax469 nm, CIEx,y=0.15, 0.22) with peak luminous efficiency of 2.15 cd/A OXD-7 (1,3-bis(2-(4-tertbutylphenyl)-1,3,4-oxadiazol-5-yl)benzene) as an electron-transporting dopant was found to improve the performance of PLED significantly. A better balanced hole/electron charge carrier was ascribed to electrontransporting, 1, 3, 4-oxadiazole-bearing copolymer (pOXD) PLED. It showed a very mild efficiency rolls off: only 0.13 cd/A luminous efficiency drops from current densities of 10-100 mA/cm2, corresponding to EL brightness of 169-1558 cd/m2.
- Chen, Hung-Yang,Chen, Chin-Ti,Chen, Chao-Tsen
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experimental part
p. 3613 - 3623
(2011/10/09)
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- BICYCLO-SUBSTITUTED PYRAZOLON AZO DERIVATIVES, PREPARATION PROCESS AND PHARMACEUTICAL USE THEREOF
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The bicyclo-substituted pyrazolon-azo derivatives of formula (I) or pharmaceutical acceptable salts, hydrates or solvates thereof, methods for their preparation, pharmaceutical compositions containing the same and their use as a therapeutic agent, especially as thrombopoietin (TPO) mimetics and their use as agonists of thrombopoietin receptor are disclosed. The definition of substituents in formula (I) are the same as defined in the description.
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Page/Page column 26
(2010/10/19)
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- Antimony trioxide as an efficient Lewis acid catalyst for the synthesis of 5-substituted 1H-tetrazoles
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Sb2O3 was found to be effective as a catalyst for a smooth (2 + 3) cycloaddition of sodium azide with nitriles to afford 5-substituted 1H-tetrazoles in good yields. Copyright Taylor & Francis Group, LLC.
- Venkateshwarlu,Rajanna,Saiprakash
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experimental part
p. 426 - 432
(2009/05/30)
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- FeCl3-SiO2 as a reusable heterogeneous catalyst for the synthesis of 5-substituted 1H-tetrazoles via [2+3] cycloaddition of nitriles and sodium azide
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An efficient method for the preparation of 5-substituted 1H-tetrazole derivatives is reported using FeCl3-SiO2 as an effective heterogeneous catalyst. This method has the advantages of high yields, simple methodology, and easy work-up. The catalyst can be recovered by simple filtration and reused delivering good yields.
- Nasrollahzadeh, Mahmoud,Bayat, Yadollah,Habibi, Davood,Moshaee, Saeed
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experimental part
p. 4435 - 4438
(2009/11/30)
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- Inhibition of the CRM1-mediated nucleocytoplasmic transport by N-azolylacrylates: Structure-activity relationship and mechanism of action
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CRM1-mediated nucleocytoplasmic transport plays an important role in many cellular processes and diseases. To investigate the structural basis required for the inhibition of the CRM1-mediated nuclear export we have synthesized analogs of a previously identified small molecule lead compound and monitored their activity against the Rev function of the human immunodeficiency virus. Microscopy studies show that the active congeners of this series inhibit the nucleocytoplasmic transport of Rev and the co-localization between Rev and CRM1 in living cells. Mechanism of action studies show their interaction with the Cys528 residue of CRM1 involving a Michael-addition type of reaction. However, structure-activity relationship demonstrates strict constraints to the structure of the inhibitors, and shows that activity is not solely correlated to Michael-addition suggesting a more complex mechanism of action. Our results are suggestive for the existence of a well-defined interaction at the CRM1-NES binding site. In addition, the most selective congener inhibited the HIV-1 production in latently infected cells. These specific CRM1 inhibitors are of interest as tool for analyzing the mechanisms of post-transcriptional control of gene expression and provide insight in the design of new agents.
- Van Neck, Tine,Pannecouque, Christophe,Vanstreels, Els,Stevens, Miguel,Dehaen, Wim,Daelemans, Dirk
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experimental part
p. 9487 - 9497
(2009/04/11)
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- THE USE OF SELECTIVE P2X7 RECEPTOR ANTAGONISTS
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The present invention relates to the use of selective P2X7 receptor antagonists of formula (I), or a pharmaceutically acceptable salt or prodrug thereof wherein D, R1 and R2 are as defined in claim 1, for the treatment of neuropathic pain, chronic inflammatory pain, inflammation, neurodegeneration and for promoting neuroregeneration.
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Page/Page column 46
(2008/06/13)
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- HETERO BIARYL DERIVATIVES AS MATRIX METALLOPROTEINASE INHIBITORS
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This invention provides compounds defined by Formula I or a pharmaceutically acceptable salt thereof, wherein Rl, Q, S, T, U, V, and R2 are as defined in the specification. The invention also provides pharmaceutical compositions comprising a compound of Formula I, or a pharmaceutically acceptable salt thereof, as defined in the specification, together with a' pharmaceutically acceptable carrier, diluent, or excipient. The invention also provides methods of inhibiting an MMP-13 enzyme in an animal, comprising administering to the animal a compound of Formula I, or a pharmaceutically acceptable salt thereof. The invention also provides methods of treating a disease mediated by an MMP-13 enzyme in a patient, comprising administering to the patient a' compound of Formula I, or a pharmaceutically acceptable salt thereof, either alone or in a pharmaceutical composition. The invention also provides methods of treating diseases such as heart disease, multiple sclerosis, osteo- and rheumatoid arthritis, arthritis other than osteo- or rheumatoid arthritis, cardiac insufficiency,,inflammatory bowel, disease, heart failure, age-related macular degeneration, chronic obstructive pulmonary disease, asthma, periodontal diseases, psoriasis, atherosclerosis, and osteoporosis in a patient, comprising administering to the patient a compound of Formula I, or a pharmaceutically, acceptable salt thereof, either alone or in a pharmaceutical composition. The invention also provides combinations, comprising a compound of Formula I, or a pharmaceutically acceptable salt thereof, together with another pharmaceutically active, component as described in the specification.
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Page/Page column 145-146
(2008/06/13)
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- Process for the preparation of tetrazoles
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The present invention relates to a process for the preparation of 5-aryl tetrazoles of the formula: STR1 or a salt thereof comprising reacting an aryl nitrile with a trisubstituted silyl azide and a disubstituted tin oxide.
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