- 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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- Fe3O4@L-lysine-Pd(0) organic–inorganic hybrid: As a novel heterogeneous magnetic nanocatalyst for chemo and homoselective [2 + 3] cycloaddition synthesis of 5-substituted 1H-tetrazoles
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An efficient and sustainable synthetic protocol has been presented to synthesis and 5-substituted 1H-tetrazole privileged heterocyclic substructures. The synthetic protocol involves two-component reaction between aryl nitriles and NaN3 in water using complex of L-lysine-palladium nanoparticles (NPs) modified Fe3O4 nanoparticles as magnetically separable, recyclable, and reusable heterogeneous catalyst. Magnetically retrievable L-lysine-Pd(0) modified Fe3O4 nanoparticles were applied in [2 + 3] cycloaddition synthesis of 5-substituted 1H-tetrazoles. The advantages of this strategy include easy recovery and efficient reusability of the expensive Pd NPs, obtaining high yields of [2 + 3] cycloaddition, short reaction times, and all of the reported synthetic strategies are being performed in water as green solvent for a wide range of substrates.
- Ashraf, Muhammad Aqeel,Liu, Zhenling,Li, Cheng,Zhang, Dangquan
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- Igneous rock powder as a heterogeneous multi-oxide nano-catalyst for the synthesis of 5-substituted-1H-tetrazoles in polyethylene glycol
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The use of igneous rock nano-powder as a heterogeneous and recyclable multi-oxide nano-catalyst synthesizing of 5-substituted-1H-tetrazoles is reported. The igneous rock nano-powder was initially prepared by using the ball-milling method. Then, the structure, morphology, and magnetic properties of the prepared igneous rock nano-powder were characterized with some different spectroscopic, microscopic, and thermogravimetric techniques, such as FTIR, FESEM, XRF, XRD, Histogram, and EDS. The instrumental analyses showed that the prepared igneous rock powder is a mixture of metal oxides, such as Si, Al, Ca, Mg, Fe, Na, Mn, and Sr. It showed an excellent catalytic performance in synthesizing of 5-substituted-1H-tetrazoles through [3 + 2] cycloaddition reaction between sodium azide and nitrile compounds. Various aliphatic and aromatic nitriles and sodium azide were reacted in the presence of a catalytic amount of igneous rock nano-powder at 80 o C temperature in PEG-400. The protocol was simple and rapid, with suitable yields of the obtained tetrazoles. The igneous rock nano-powder is readily accessible, reusable, and holds potential for further application in acid-catalyzed organic syntheses and industrial requirements. Graphic abstract: [Figure not available: see fulltext.]
- Javaherian, Mohammad,Movaheditabar, Parviz,Nobakht, Valiollah
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- BENZIMIDAZOLE COMPOUNDS AND USE THEREOF FOR TREATING ALZHEIMER'S DISEASE OR HUNTINGTON'S DISEASE
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Benzimidazole compounds of formula (I), shown below, are disclosed. The compounds are potent human glutaminyl cyclase inhibitors. Also disclosed is a pharmaceutical composition containing one of these compounds and a pharmaceutical acceptable carrier, as well as a method of treating Alzheimer's disease or Huntington's disease by administering to a subject in need thereof an effective amount of such a compound.
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Page/Page column 13; 25; 26; 85
(2020/03/23)
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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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supporting information
(2020/01/21)
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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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- Boehmite@SiO2@ Tris (hydroxymethyl)aminomethane-Cu(I): a novel, highly efficient and reusable nanocatalyst for the C-C bond formation and the synthesis of 5-substituted 1H-tetrazoles in green media
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In this work, a versatile protocol was introduced for the preparation of a new Cu(I) supported complex on Silica supported boehmite nanoparticles (Boehmite@SiO2@Tris-Cu(I)). The structure of the catalyst was comprehensively characterized using
- Ghorbani-Choghamarani, Arash,Aghavandi, Hamid,Mohammadi, Masoud
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- Guanidine complex of copper supported on boehmite nanoparticles as practical, recyclable, chemo and homoselective organic–inorganic hybrid nanocatalyst for organic reactions
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Boehmite (BO) nanoparticles (NPs) were prepared via the injection of aqueous NaOH solution to aqueous aluminum nitrate solution at room temperature. Afterwards, a new complex of copper was immobilized on BO-NPs (Cu-Guanidine@BO-NPs). This heterogeneous nanocatalyst was used as a practical, recyclable, chemo and homoselective nanocatalyst in the organic processes, i.e. the preparation of tetrazole five-membered heterocycles and chemoselective sulfoxidation of sulfides using H2O2 as oxidant. In this sense, the prepared nanocatalyst was characterized by AAS, N2 adsorption–desorption isotherms, WDX, EDS, SEM, and TGA techniques. The reusability of this catalyst was investigated in the described organic reactions for several runs without notable loss of its catalytic activity. Moreover, all of the tetrazole and sulfoxide derivatives were isolated in high Turn Over Number (TON) and Turn Over Frequency (TOF) numbers indicating the high activity and selectivity of Cu-Guanidine@BO-NPs in the described reactions.
- Jafari, Fariba,Ghorbani-Choghamarani, Arash,Hasanzadeh, Neda
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- Fabricated copper catalyst on biochar nanoparticles for the synthesis of tetrazoles as antimicrobial agents
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Biochar is a carbon-rich solid which its surface was covered by high density of carbonyl, hydroxyl and carboxylic acid functional groups. In this work, biochar nanoparticles were prepared from pyrolysis of chicken manure and further a new copper catalyst
- Moradi, Parisa,Hajjami, Maryam,Tahmasbi, Bahman
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- Copper and nickel immobilized on cytosine@MCM-41: as highly efficient, reusable and organic–inorganic hybrid nanocatalysts for the homoselective synthesis of tetrazoles and pyranopyrazoles
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In this work, a green approach is reported for efficient synthesis of biologically active tetrazole and pyranopyrazole derivatives in the presence of Cu-Cytosine@MCM-41 and Ni-Cytosine@MCM-41 (copper (II) and nickel (II) catalyst on the modified MCM-41 us
- Nikoorazm, Mohsen,Tahmasbi, Bahman,Gholami, Shahab,Moradi, Parisa
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- Palladium fabricated on boehmite as an organic-inorganic hybrid nanocatalyst for C-C cross coupling and homoselective cycloaddition reactions
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Herein, boehmite nanoparticles were prepared using an aqueous solution of NaOH and Al(NO3)3?9H2O at room temperature. After modification of the boehmite nanoparticle (BNP) surface by 3-choloropropyltrimtoxysilane (CPTMS), adenine was anchored on the surface. Finally, a complex of palladium was fabricated on the BNP surface (Pd-adenine@boehmite). The obtained nanoparticles were identified by TGA, FT-IR, BET, EDS, WDX, SEM, XRD and AAS techniques. In continuation, the Pd-adenine@boehmite was employed as an efficient, reusable and organic-inorganic hybrid catalyst in the C-C cross coupling reactions without a phosphine ligand or an inert atmosphere. Moreover, the homoselective synthesis of tetrazoles was studied in the presence of Pd-adenine@boehmite as a heterogeneous and practical nanocatalyst which can be recovered and reused in the described organic reactions. Besides, organic products which were isolated in suitable TOF and TON numbers in the presence of Pd-adenine@boehmite as a catalyst revealed the practicality of this catalyst. The heterogeneous nature of this catalyst was confirmed by TEM, EDS, WDX, AAS, and FT-IR techniques and, then, compared to the fresh catalyst.
- Tahmasbi, Bahman,Ghorbani-Choghamarani, Arash,Moradi, Parisa
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p. 3717 - 3727
(2020/03/17)
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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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- Tandem magnetization and post-synthetic metal ion exchange of metal–organic framework: Synthesis, characterization and catalytic study
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For the first time, metal-exchange in a magnetic metal–organic framework (MOF) via tandem magnetization and post-synthetic modification has been developed. The new magnetic mixed-metal metal–organic framework nanocomposite, CoFe2O4/[
- Yadollahi, Mahtab,Hamadi, Hosein,Nobakht, Valiollah
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- Core–shell nanostructure (Fe3O4?MCM-41?Cu-P2C) as a highly efficient and recoverable nanocatalyst for the synthesis of polyhydroquinoline, 5-substituted 1H-tetrazoles and sulfides
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Fe3O4 magnetic nanoparticles were used as a core for Cu(II) Schiff base complex functionalized mesoporous MCM-41 shell to provide a core–shell nanostructure (Fe3O4?MCM-41?Cu-P2C). A simple, environmentally friendly, inexpensive, green reaction conditions and efficient procedure for the synthesis of polyhydroquinoline, 5-substituted 1H-tetrazoles and sulfides derivatives using this core–shell nanostructure as an efficient, novel and recoverable nanocatalyst has been described. Fe3O4?MCM-41?Cu-P2C is stable, cost-effective, heterogeneous, easy to handle and recoverable nanocatalyst and can be reused for several consecutive runs without a significant loss of catalytic activity. The catalyst was characterized by fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), powder X-ray diffractometer (XRD), scanning electron microscopy (SEM), atomic absorption spectroscopy (AAS), Brunauer–Emmett–Teller (BET) and vibrating sample magnetometer (VSM) techniques.
- Nikoorazm, Mohsen,Erfani, Zahra
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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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- 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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- 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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- An efficient and recyclable catalytic system for carbon–sulfur coupling reaction and synthesis of 5-substituted 1H-tetrazoles
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In this research paper, efficient and economical protocols for the synthesis of symmetrical sulfides and 5-substituted 1H-tetrazoles have been reported using Fe3O4@SBTU@Ni(II) as a heterogeneous and recoverable nanocatalyst. The noticeable features of this catalytic system are: operational simplicity, environmentally benign, easier work-up procedure, green and efficient synthetic entry to excellent yield of products in a high reusability and applicability to various starting materials and, therefore, cost efficiency.
- Ghorbani-Choghamarani, Arash,Moradi, Zahra,Azadi, Gouhar
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p. 237 - 251
(2018/01/04)
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- A new Pd-Schiff-base complex on boehmite nanoparticles: Its application in Suzuki reaction and synthesis of tetrazoles
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Boehmite nanoparticles are not air or moisture sensitive, therefore have been prepared in water without inert atmosphere using inexpensive materials. Pd-isatin-boehmite was synthesized and used as heterogeneous organometallic catalyst for the synthesis of 5-substituted 1H-tetrazoles and C-C band formation. Pd-isatin-boehmite characterized by XRD, TGA, SEM and ICP-OES techniques. This catalyst was reused for several times without significant loss of its catalytic efficiency or palladium leaching. Heterogeneity of this catalyst has been studied using ICP-OES technique.
- Jabbari, Arida,Tahmasbi, Bahman,Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash
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- Anchoring of Cu(II)–vanillin Schiff base complex on MCM-41: A highly efficient and recyclable catalyst for synthesis of sulfides and 5-substituted 1H–tetrazoles and oxidation of sulfides to sulfoxides
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A copper(II)–vanillin complex was immobilized onto MCM-41 nanostructure and was used as an inexpensive, non-toxic and heterogeneous catalyst in the synthesis of symmetric aryl sulfides by the cross-coupling of aromatic halides with S8 as an effective sulfur source, in the oxidation of sulfides to sulfoxides using 30% H2O2 as a green oxidant and in the synthesis of 5-substituted 1H–tetrazoles from a smooth (3?+?2) cycloaddition of organic nitriles with sodium azide (NaN3). The products were obtained in good to excellent yields. This catalyst could be reused several times without loss of activity. Characterization of the catalyst was performed using Fourier transform infrared, energy-dispersive X-ray and atomic absorption spectroscopies, X-ray diffraction, thermogravimetric analysis, and scanning and transmission electron microscopies.
- Khanmoradi, Maryam,Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash
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- Copper(II) immobilized on Fe3O4@SiO2@l-Histidine: a reusable nanocatalyst and its application in the synthesis of 5-substituted 1H-tetrazoles
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Herein, we report the synthesis and application of Cu(II) immobilized on Fe3O4@SiO2@l-Histidine, which was characterized by FTIR spectroscopy, X-ray diffraction, thermogravimetric analysis, scanning electron microscopy and
- Azadi, Gouhar,Ghorbani-Choghamarani, Arash,Shiri, Lotfi
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p. 131 - 136
(2017/02/23)
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- First report of the direct supporting of palladium–arginine complex on boehmite nanoparticles and application in the synthesis of 5-substituted tetrazoles
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Boehmite nanoparticles are aluminium oxide hydroxide (γ-AlOOH) particles, which were prepared using a simple and inexpensive procedure in water at room temperature and further modified using arginine. Subsequently palladium particles were immobilized on their surface to prepare Pd-Arg@boehmite. This novel nanostructured compound was fully characterized using thermogravimetric analysis, X-ray diffraction, inductively coupled plasma optical emission (ICP-OES) and energy-dispersive X-ray spectroscopies, and scanning and transmission electron microscopies. Finally, this catalyst was applied as a moisture- and air-stable heterogeneous material for the synthesis of 5-substituted 1H–tetrazole derivatives. The leaching of palladium and heterogeneity of the catalyst were studied using hot filtration and ICP-OES. This catalyst demonstrated remarkable recyclability. The novelty of this work is that it represents the first time an amino acid has been grafted on boehmite nanoparticles.
- Tahmasbi, Bahman,Ghorbani-Choghamarani, Arash
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- Pd-SBT@MCM-41: As an efficient, stable and recyclable organometallic catalyst for C-C coupling reactions and synthesis of 5-substituted tetrazoles
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A palladium S-benzylisothiourea complex was anchored on functionalized MCM-41 (Pd-SBT@MCM-41) and applied as efficient and reusable catalyst for the synthesis of 5-substituted 1H–tetrazoles using [2?+?3] cycloaddition reaction of various organic nitriles with sodium azide (NaN3) in poly(ethylene glycol) (PEG) as green solvent. Also this catalyst was applied as an versatile organometallic catalyst for Suzuki cross-coupling reaction of aryl halides and phenylboronic acid (PhB(OH)2) or sodium tetraphenyl borate (NaB(Ph)4). This nanocatalyst was characterized by thermal gravimetric analysis (TGA), X-ray Diffraction (XRD), scanning electron microscopy (SEM), inductively Coupled Plasma (ICP) and N2 adsorption–desorption isotherms techniques. Recovery of the catalyst is easily achieved by centrifugation for several consecutive runs.
- Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash,Ghobadi, Massoud,Massahi, Shokofeh
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- High Catalytic Activity of Peptide Nanofibres Decorated with Ni and Cu Nanoparticles for the Synthesis of 5-Substituted 1H-Tetrazoles and N-Arylation of Amines
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A rapid development of a new methodology for decarboxylative N-arylation of carboxylic acids and the preparation of 5-substituted 1H-tetrazoles catalysed by peptide nanofibres decorated with Cu and Ni nanoparticles is presented. Compared with conventional aryl halides, benzoic acids are extremely interesting and environmentally friendly options for the synthesis of secondary aryl amines.
- Ghorbani-Choghamarani, Arash,Taherinia, Zahra
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p. 1127 - 1137
(2017/10/10)
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- Antimicrobial evaluation of 5-substituted aryl 1H-tetrazoles
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Background: Tetrazole derivatives such as 1-substituted dinitrobenzyl tetrazoles and their oxa and selanyl analogs have previously been studied against drug-susceptible and multidrugresistant mycobacteria. In addition, other tetrazole derivatives have bee
- Feinn, Liana,Dudley, Joshua,Coca, Adiel,Roberts, Elizabeth L.
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p. 359 - 364
(2017/06/20)
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- Computer design, synthesis, and bioactivity analyses of drugs like fingolimod used in the treatment of multiple sclerosis
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Multiple sclerosis (MS) is a very common disease of vital importance. In the MS treatment, some drugs such as fingolimod which help to protect nerves from damage are used. The main goal of the drug therapy in MS is to take control of the inflammation whic
- Turgut, Gurbet ?elik,Doyduk, Do?ukan,Y?ld?r?r, Y?lmaz,Yavuz, Serkan,Akdemir, Atilla,Di?li, Ali,?en, Alaattin
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p. 483 - 495
(2016/12/30)
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- Efficient synthesis of 5-substituted tetrazoles catalysed by palladium–S-methylisothiourea complex supported on boehmite nanoparticles
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An efficient and general method is reported for the synthesis of 5-substituted 1H-tetrazole derivatives in the presence of S-methylisothiourea complex of palladium immobilized on boehmite nanoparticles (Pd-SMTU@boehmite) as an efficient and recyclable nan
- Moradi, Parisa,Ghorbani-Choghamarani, Arash
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- Conversion of Arylboronic Acids to Tetrazoles Catalyzed by ONO Pincer-Type Palladium Complex
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A convenient synthesis of a library of tetrazoles through a novel and operationally simple protocol effecting the direct conversion of arylboronic acids catalyzed by a new ONO pincer-type Pd(II) complex under mild reaction conditions using the readily available reagents is reported. The palladium complex was reused up to four cycles in an open-flask condition.
- Vignesh, Arumugam,Bhuvanesh, Nattamai S. P.,Dharmaraj, Nallasamy
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p. 887 - 892
(2018/06/15)
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- A comparative study between heterogeneous stannous chloride loaded silica nanoparticles and a homogeneous stannous chloride catalyst in the synthesis of 5-substituted 1: H -tetrazole
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Heterogeneous SnCl2-nano-SiO2 efficiently catalyzed 5-substituted 1H-tetrazole synthesis with excellent yield. The catalyst was characterized by using FT-IR, TGA, TEM, and EDX. It is widely applicable on aliphatic, aromatic, heteroaromatic and sterically hindered nitriles with five time recyclability. Being simple and an economically viable approach for the synthesis of SnCl2-nano-SiO2 are additional advantages.
- Kumar, Arvind,Kumar, Satyanand,Khajuria, Yugal,Awasthi, Satish Kumar
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p. 75227 - 75233
(2016/08/24)
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- Ni-S-methylisothiourea complexes supported on boehmite nanoparticles and their application in the synthesis of 5-substituted tetrazoles
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Boehmite nanoparticles are aluminum oxide hydroxide (γ-AlOOH) particles, which were prepared by a simple and inexpensive procedure and immobilized further with nickel-S-methylisothiourea complexes (Ni-SMTU@boehmite), and characterized by FT-IR spectroscopy, TGA, XRD, ICP-OES, EDS, SEM and TEM techniques. Finally, we investigated the catalytic activity of Ni-SMTU@boehmite as a new, heterogeneous, stable and highly reusable nanocatalyst for the synthesis of 5-substituted 1H-tetrazole derivatives in PEG-400 as a green solvent. This catalyst was recovered by simple filtration and reused several times without significant loss of its catalytic efficiency or nickel leaching. The heterogeneity of this catalyst has been studied using hot filtration and ICP-OES technique.
- Ghorbani-Choghamarani, Arash,Moradi, Parisa,Tahmasbi, Bahman
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p. 56638 - 56646
(2016/07/06)
-
- Application of Pd-2A3HP-MCM-41 to the Suzuki, Heck and Stille coupling reactions and synthesis of 5-substituted 1H-tetrazoles
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An ecofriendly heterogeneous catalyst has been synthesized by anchoring palladium onto the surface of organically modified mesoporous silica. The prepared catalyst was characterized using X-ray diffraction, Fourier transform infrared and energy-dispersive X-ray spectroscopies, transmission and scanning electron microscopies, inductively coupled plasma and thermogravimetric techniques. The catalyst shows high activity in the Suzuki, Heck and Stille cross-coupling reactions and the synthesis of 5-substituted 1H-tetrazoles from sodium azide (NaN3). These methods have the advantages of high yields, green reaction conditions, simple methodology and easy separation and workup.
- Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash,Khanmoradi, Maryam
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p. 705 - 712
(2016/07/19)
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- Activated Fuller's earth as an inexpensive, eco-friendly, efficient catalyst for the synthesis of 5-aryl 1-H-tetrazole via [3+2] cycloaddition of nitriles and sodium azide
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A simple and efficient method for the preparation of 5-aryl 1-H-tetrazoles was developed from various aryl nitriles and sodium azide (NaN3) via [3+2] cycloaddition reaction using activated Fuller's earth as an efficient heterogeneous catalyst.
- Rekunge, Deelip S.,Indalkar, Krishna S.,Chaturbhuj, Ganesh U.
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supporting information
p. 5815 - 5819
(2016/12/06)
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- The first report on the eco-friendly synthesis of 5-substituted 1: H -tetrazoles in PEG catalyzed by Cu(ii) immobilized on Fe3O4@SiO2@l-arginine as a novel, recyclable and non-corrosive catalyst
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Cu(ii) immobilized on Fe3O4@SiO2@l-aginine as a novel, inexpensive and non-corrosive nanostructured compound catalyzed the cycloaddition reaction of various organic nitriles with sodium azide. This combination leads to obt
- Ghorbani-Choghamarani, Arash,Shiri, Lotfi,Azadi, Gouhar
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p. 32653 - 32660
(2016/05/09)
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- 5-SUBSTITUTED 1 H-TETRAZOLE COMPOUNDS, METHODS OF SYNTHESIZING AND THERAPEUTIC USE
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A pharmaceutical formulation includes an antibiotic 5-substituted 1H-tetrazole compound in an amount sufficient to treat a bacterial infection, the antibiotic 5-substituted 1H-tetrazole compound being selected from the group consisting of: an aryl tetrazo
- -
-
Paragraph 0020; 0021
(2016/12/07)
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- Facile synthesis of 5-substituted 1H-tetrazoles catalyzed by tetrabutylammonium hydrogen sulfate in water
-
Facile synthesis of 5-substituted 1H-tetrazoles was achieved by treating nitriles with NaN3 in water or toluene in the presence of tetrabutylammoniumhydrogen sulfate (TBAHS). The reaction could be carried out in water as well as in toluene. The
- Wang, Zengtao,Liu, Zhiguo,Cheon, Seung Hoon
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p. 198 - 202
(2015/03/03)
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- Highly efficient synthesis of 5-substituted 1H-tetrazoles catalyzed by Cu-Zn alloy nanopowder, conversion into 1,5- and 2,5-disubstituted tetrazoles, and synthesis and NMR studies of new tetrazolium ionic liquids
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A series of 5-substituted 1H-tetrazoles were synthesized through [3+2] cycloaddition reactions between nitriles RCN and NaN3 in the presence of Cu-Zn alloy nanopowder as catalyst. The 1,5-dibutyl, 1-butyl-5-hexyl, 2,5-dibutyl, and 2-butyl-5-hexyl derivatives were then used as building blocks to synthesize several novel tetrazolium ionic liquids (ILs) with EtSO 4-, OTf-, and NTf2- counterions. Whereas alkylation of the 2,5-dialkyltetrazoles selectively gave the N-4 alkylated onium salts, with the 1,5-dialkyl derivatives approximately 1:1 mixtures of two tetrazolium salts were formed by alkylation at N-3 and N-4. The triflate and ethyl sulfate salts are room-temperature ILs that are hydrophilic, whereas the NTf2 salts are low-melting ILs and are hydrophobic. The resulting tetrazolium-based ionic liquids were studied by various multinuclear and 2D NMR techniques including natural abundance 15N and 1H/15N correlations.
- Aridoss, Gopalakrishnan,Laali, Kenneth K.
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experimental part
p. 6343 - 6355
(2011/12/03)
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- One-pot synthesis of 5-substituted lH-tetrazoles from aryl bromides with potassium hexakis(cyano-κC)ferrate(4 -)(K4[Fe(CN)6]) as cyanide source
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A one-pot procedure for the synthesis of 5-substituted 1H-tetrazoles through the three-component reaction between an aryl bromide, potassium hexakis(cyano-κC)ferrate(4 - ) (K4[Fe(CN)6]) and NaN3 catalyzed by [Pd(OAc)2
- Zhu, Yizhong,Ren, Yiming,Cai, Chun
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experimental part
p. 171 - 175
(2009/05/30)
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- Amberlite IRA900F as a solid fluoride source for a variety of organic transformations under solvent-free conditions
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We have reported that Amberlite IRA900F (Amb-F) is an efficient metal-free catalyst for the activation of Si-N and Si-O bonds and a mild base in a variety of organic transformations under solvent-free conditions, such as the addition of TMSN3 to (E)-2-aryl-1-cyano-1-nitroethenes, nitriles, α,β-unsaturated acids and their esters, and the addition of dimethylsilyl ketene acetal and ethyl nitroacetate to β-nitrostyrenes. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Fringuelli, Francesco,Lanari, Daniela,Pizzo, Ferdinando,Vaccaro, Luigi
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experimental part
p. 3928 - 3932
(2009/04/08)
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- 5-Aryltetrazole Compounds, compositions thereof, and uses therefor
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The present invention relates to 5-Aryltetrazole compounds, compositions comprising a 5-Aryltetrazole compound, and methods for treating an inflammation disease, a reperfusion disease, hyperuricemia, gout, or tumor-lysis syndrome in an animal in need ther
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- TBAF-Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles under Solventless Conditions
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Tetrabutylammonium fluoride (TBAF) is an efficient catalyst in the [3 + 2] cycloaddition reaction of organic nitriles 1 with trimethylsilyl azide (TMSN3) in solventless conditions. The corresponding 5-substituted 1H-tetrazoles 2 were obtained under mild conditions and in 80-97% yields.
- Amantini, David,Beleggia, Romina,Fringuelli, Francesco,Pizzo, Ferdinando,Vaccaro, Luigi
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p. 2896 - 2898
(2007/10/03)
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- Antibacterial chalcones - Bioisosteric replacement of the 4′-hydroxy group
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Hydroxy chalcones, for example, Licochalcone A, has for several years been known to be antibacterial. The low aqueous solubility and the medium antibacterial potency have limited the usefulness of the compounds. We describe the bioisosteric replacement of
- Nielsen, Simon Feldbaek,Boesen, Thomas,Larsen, Mogens,Schonning, Kristian,Kromann, Hasse
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p. 3047 - 3054
(2007/10/03)
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