cas 51517-88-5, 4-(2-TRITYL-2H-TETRAZOL-5-YLMETHYL)-PHENOL

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Variation in hydrophobic chain length of co-adsorbents to improve dye-sensitized solar cell performance
Three compounds based on the phenyltetrazole system, 5-(4-hydroxyphenyl)tetrazole (LTz-1), 5-(4-methoxyphenyl)tetrazole (LTz-2) and 5-(4-hexyloxyphenyl)tetrazole (LTz-3), were synthesized and characterized as co-adsorbents in dye-sensitized solar cells (DSSCs). The effects of hydrophobic chain length of the co-adsorbent and the effects of tetrazole anchoring group on the properties of DSSCs containing the previously reported dye HD-2 were compared with the benchmark deoxycholic acid (DCA). The charge-transfer resistance of the dye/TiO2 interface followed the order HD-2-DCA > HD-2-LTz-2 > HD-2-LTz-3 > HD-2-LTz-1. However, the Voc of the dye HD-2 with co-adsorbent DCA was 0.66 V, for the dye HD-2 with co-adsorbent LTz-1, it was 0.70 V, for the dye HD-2 with co-adsorbent LTz-2, it was 0.68 V and for the dye HD-2 with co-adsorbent LTz-3, it was 0.67 V. Co-adsorbents LTz-1, LTz-2 and LTz-3 achieved a mean solar-to-power conversion efficiency (%η), for the three devices, of 8.29, 7.63 and 8.49, respectively, compared to 7.76 for DCA under the same experimental device conditions. For the LTz-3 co-adsorbent, the results can be attributed to the repellent effect of the long alkyl chain. For LTz-1 and LTz-2 co-adsorbents, it is possible that the more compact layer formed improves electron-injection efficiency into TiO2.
Da Silva, Luciano,Freeman, Harold
p. 16771 - 16778
(2019)
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Photophysical and biological investigation of phenol substituted rhenium tetrazolato complexes
The synthesis, structural and photophysical characterisation of four tricarbonyl rhenium(i) complexes bound to 1,10-phenanthroline and a tetrazolato ancillary ligand are reported. The complexes are differentiated by the nature (hydroxy or methoxy) and pos
Akabar, Nurshadrina,Chaturvedi, Vishal,Shillito, Georgina E.,Schwehr, Bradley J.,Gordon, Keith C.,Huff, Gregory S.,Sutton, Joshua J.,Skelton, Brian W.,Sobolev, Alexandre N.,Stagni, Stefano,Nelson, Delia J.,Massi, Massimiliano
p. 15613 - 15624
(2019)
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CuO–NiO bimetallic nanoparticles supported on graphitic carbon nitride with enhanced catalytic performance for the synthesis of 1,2,3-triazoles, bis-1,2,3-triazoles, and tetrazoles in parts per million level
The unification of CuCl2·2H2O and NiCl2·6H2O with the support of graphitic carbon nitride yielded to form an efficient, synergistic, bimetallic nano-catalyst CuO–NiO@g-C3N4. FT-IR, SEM, TEM
Gajurel, Sushmita,Dam, Binoyargha,Bhushan, Mayank,Singh, L. Robindro,Pal, Amarta Kumar
(2021/12/09)

Synthesis and characterization of magnetic Fe3O4@Creatinine@Zr nanoparticles as novel catalyst for the synthesis of 5-substituted 1H-tetrazoles in water and the selective oxidation of sulfides with classical and ultrasonic methods
Tetrazoles and sulfoxide compounds have a wide range of applications in industries and are of great expectation to be environmentally friendly and cost-effective. This paper reports the introduction of zirconium supported on Fe3O4 na
Ghadermazi, Mohammad,Moeini, Nazanin,Molaei, Somayeh
(2021/12/03)

Catalytic conversion of 2,4,5-trisubstituted imidazole and 5-substituted 1H-tetrazole derivatives using a new series of half-sandwich (η6-p-cymene)Ruthenium(II) complexes with thiophene-2-carboxylic acid hydrazone ligands
A new series of half-sandwich (η6-p-cymene) ruthenium(II) complexes with thiophene-2-carboxylic acid hydrazide derivatives [Ru(η6-p-cymene)(Cl)(L)] [L = N'-(naphthalen-1-ylmethylene)thiophene-2-carbohydrazide (L1), N'-(anthracen-9-ylmethylene)thiophene-2-carbohydrazide (L2) and N'-(pyren-1-ylmethylene)thiophene-2-carbohydrazide (L3)] were synthesized. The ligand precursors and their Ru(II) complexes (1–3) were structurally characterized by spectral (IR, UV–Vis, NMR and mass spectrometry) and elemental analysis. The molecular structures of the ruthenium(II) complexes 1–3 were determined by single-crystal X-ray diffraction. All complexes were used as catalysts for the one-pot three-component syntheses of 2,4,5-trisubstitued imidazole and 5-substituted 1H-tetrazole derivatives. The catalytic studies optimized parameters as solvent, temperature and catalyst. The catalysts revealed very active for a broad range of aromatic aldehydes presenting either electron attractor or electron donor substituents and, although less active, moderate to high activities were observed for alkyl aldehydes.
Vinoth, Govindasamy,Indira, Sekar,Bharathi, Madheswaran,Archana, Govindhasamy,Alves, Luis G.,Martins, Ana M.,Shanmuga Bharathi, Kuppannan
(2020/11/16)

Synthesis, X-ray characterization, Hirshfeld surface analysis and DFT calculations on tetrazolyl-phenol derivatives: H-bonds vs C–H…π/π…π interactions
Tetrazoles are nitrogen rich heterocycles with a broad spectrum of medicinal properties and potential for use as drugs. A significant number of FDA approved drugs incorporate the tetrazole moiety indicating the versatile pharmaceutical potential associate
Bibi, Asma,Khan, Imtiaz,Andleeb, Hina,Simpson, Jim,Tahir, Muhammad Nawaz,Hameed, Shahid,Frontera, Antonio
(2020/10/20)

Sustainable and recyclable magnetic nanocatalyst of 1,10-phenanthroline Pd(0) complex in green synthesis of biaryls and tetrazoles using arylboronic acids as versatile substrates
A magnetic nanocatalyst was purveyed as a heterogeneous recoverable palladium-based catalyst anchored on green, sustainable and phosphine free support. Resulted Fe3O4@SiO2-Phen-Pd(0) nanocatalyst bearing powerful phenanthroline ligand was thoroughly characterized by physicochemical approaches like UV–vis, FT-IR, EDX, XRD, TGA, ICP, VSM, DLS, FESEM, and TEM analyses. After finding trustable data, the obtained magnetic catalyst was considered to be applied in the Suzuki-Miyaura type C-C couplings and getting corresponding tetrazoles using arylboronic acid derivatives as alternate precursors of aromatic halides and stupendous data were observed.
Bagherzadeh, Nastaran,Sardarian, Ali Reza,Eslahi, Hassan
(2021/04/02)

Oxidation/ MCR domino protocol for direct transformation of methyl benzene, alcohol, and nitro compounds to the corresponding tetrazole using a three-functional redox catalytic system bearing TEMPO/Co(III)-porphyrin/ Ni(II) complex
A redox catalytic system for oxidation-reduction reactions and the domino preparation of tetrazole compounds from nitro and alcohol precursors was designed, prepared and characterized by UV–vis, GPC, TGA, XRD, EDX, XPS, VSM, FE-SEM, TEM, DLS, BET, NMR, and ICP analyses. The catalyst was prepared via several successive steps by demetalation of chlorophyll b, copolymerization with acrylated TEMPO monomers, complexation with Ni and Co metals (In two different steps), then immobilized on magnetic nanoparticles. The presence of three functional groups including TEMPO, coordinated cobalt, and coordinated nickel in the catalyst, allowed the oxidation of various types of alcohols, alkyl benzenes as well as the reduction of nitro compounds by a single catalyst. All reactions yielded up to 97 % selectivity for oxidation and reduction reactions. Next, the ability of the catalyst to successfully convert alcohol, methyl benzenes and nitro to their corresponding tetrazoles was studied.
Mahmoudi, Boshra,Rostami, Amin,Kazemnejadi, Milad,Hamah-Ameen, Baram Ahmed
(2020/12/21)

The anchoring of a Cu(ii)-salophen complex on magnetic mesoporous cellulose nanofibers: green synthesis and an investigation of its catalytic role in tetrazole reactions through a facile one-pot route
Today, most synthetic methods are aimed at carrying out reactions under more efficient conditions and the realization of the twelve principles of green chemistry. Due to the importance and widespread applications of tetrazoles in various industries, especially in the field of pharmaceutical chemistry, and the expansion of the use of nanocatalysts in the preparation of valuable chemical reaction products, we decided to use an (Fe3O4@NFC@NSalophCu)CO2H nanocatalyst in this project. In this study, the synthesis of the nanocatalyst (Fe3O4@NFC@NSalophCu)CO2H was explained in a step-by-step manner. Confirmation of the structure was obtained based on FT-IR, EDX, FE-SEM, TEM, XRD, VSM, DLS, TGA, H-NMR, and CHNO analyses. The catalyst was applied to the synthesis of 5-substituted-1H-tetrazole and 1-substituted-1H-tetrazole derivatives through multi-component reactions (MCRs), and the performance was assessed. With advances in science and technology and increasing environmental pollution, the use of reagents and methods that are less dangerous for the environment has received much attention. Therefore, following green chemistry principles, with the help of the (Fe3O4@NFC@NSalophCu)CO2H salen complex as a nanocatalyst that is recyclable, cheap, safe, and available, the use of water as a green solvent, and reduced reaction times, the synthesis of tetrazoles can be achieved.
Bagherzade, Ghodsieh,Ghamari kargar, Pouya
p. 19203 - 19220
(2021/06/03)

Magnetic nitrogen-doped carbon derived from silk cocoon biomass: a promising and sustainable support for copper
In this study, a magnetic nitrogen-doped carbon-based copper (MNC-Cu) catalyst was fabricated so that natural silk cocoons undergo thermal processes and then activate by combining with Fe3O4 MNPs as a suitable substrate for placement copper metal. The efficiency of the generated catalyst in the synthesis of 5-substituted 1H-tetrazole derivatives was evaluated by the [3 + 2] cycloaddition reaction of aromatic aldehydes, azide ions, and hydroxylamines. FT-IR, FE-SEM, EDS, TEM, XRD, TGA, and VSM techniques have been adopted to identify and validate this heterogeneous catalyst. The observation from EDS, elemental mapping, XRD, and FT-IR analysis confirms the immobilization of Cu metals on the MNC surface and uniform distribution of species and then no aggregation occurs during functionalization. VSM results show the magnetic feature of fabricated catalyst, and based on the leaching test, the amount of catalyst leaching was negligible. Moreover, this reaction is a one-pot multicomponent reaction (MCRs) or more precisely a one-pot, three-component reaction, which is one of the advantages of this work. The fabricated catalyst shows high efficiency, good stability, and considerable reactivity in synthesizing 5-substituted 1H-tetrazole derivatives. So it can be seen that the fabricated magnetic catalyst is a useful and practical catalyst for synthesizing [3 + 2] cycloaddition reactions. Reusability and recyclability for five sequential runs without notable increase and reduction in activity are other advantages. In addition, the magnetic properties of this heterogeneous catalyst led to easy and quickly recovered and striking copper leaching. Graphical abstract: [Figure not available: see fulltext.]
Akbarzadeh, Parisa,Koukabi, Nadiya,Tahmasbi, Marzieh
(2021/12/01)

Magnetization of biochar nanoparticles as a novel support for fabrication of organo nickel as a selective, reusable and magnetic nanocatalyst in organic reactions
Catalyst species are an important class of materials in chemistry, industry, medicine and biotechnology. Also, waste recycling is an important process in green chemistry and economic efficiency. Therefore, in order to recycle waste, biochar nanoparticles were prepared from chicken manure. Then, the biochar nanoparticles were magnetized under a green and environmentally friendly method. Finally, the surface of the magnetic biochar nanoparticles was modified and further they were applied as a novel support for fabrication of nickel as a homoselective and reusable catalyst in organic reactions. The structure of this organic-inorganic catalyst has been characterized by N2adsorption-desorption isotherms, and the SEM, EDS, WDX, XRD, TGA, AAS, FT-IR and VSM techniques. This magnetically recyclable catalyst was used in the homoselective synthesis of tetrazole and pyranopyrazole derivatives. This catalyst can be reused several times without significant loss of its catalytic efficiency. The heterogeneity and stability of this nanocatalyst were studied by hot filtration and the AAS technique. Also, the reused catalyst was characterized by the SEM, EDS, AAS and BET techniques.
Moradi, Parisa,Hajjami, Maryam
p. 2981 - 2994
(2021/02/26)

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
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
(2020/12/23)

An efficient Cu/functionalized graphene oxide catalyst for synthesis of 5-substituted 1H-tetrazoles
The copper nanoparticles (Cu NPs) and amide functionalized graphene oxide (Cu-Amd-RGO) catalyst were prepared. This prepared catalyst (Cu-Amd-RGO) used for the synthesis of tetrazole derivatives. The catalyst (Cu-Amd-RGO) was characterized by field emission scanning electron microscopy (FE-SEM), transmission electron microscopy (TEM), Fourier transform infrared spectroscopy (FTIR), and X-ray diffraction analysis (XRD). The average particle size of Cu was found to be 7.6?nm. The Cu-Amd-RGO catalyst exhibited excellent catalytic activity and recyclability for synthesis of tetrazoles.
Kulkarni, Padmakar A.,Satpati, Ashis Kumar,Thandavarayan, Maiyalagan,Shendage, Suresh S.
p. 2891 - 2899
(2021/02/12)

Synthesis of 5-Substituted 1H-Tetrazoles Catalyzed by M-SAPO-34 (M = Co, Cu, Mn, Fe, and V) Nanostructures
Abstract: The synthesis of 5-substituted 1H-tetrazoles by use of a series of M-SAPO-34 (M = Co, Cu, Mn, Fe, and V) nanocatalysts are presented. Following the optimized conditions, Co-SAPO-34 nanocatalyst has been found to effectively catalyze the 5-substi
Baghershiroudi, Mahrokh,Bafandeh, Fereshteh Taghipour,Safa, Kazem D.,Panahi, Parvane Nakhostin
p. 230 - 236
(2021/04/09)

Igneous rock powder as a heterogeneous multi-oxide nano-catalyst for the synthesis of 5-substituted-1H-tetrazoles in polyethylene glycol
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
(2021/10/25)

INHIBITORS OF NOTCH SIGNALLING PATHWAY AND USE THEREOF IN TREATMENT OF CANCERS
The present invention relates to new inhibitors of Notch signalling pathway and its use in the treatment and/or prevention of cancers.
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(2020/10/21)

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
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
(2020/07/13)

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
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
(2020/07/15)

Guanidine complex of copper supported on boehmite nanoparticles as practical, recyclable, chemo and homoselective organic–inorganic hybrid nanocatalyst for organic reactions
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
(2020/08/05)

Synthesis of 5-substituted 1H-tetrazoles and oxidation of sulfides by using boehmite nanoparticles/nickel-curcumin as a robust and extremely efficient green nanocatalyst
Nickel-anchored curcumin-functionalized boehmite nanoparticles (BNPs@Cur-Ni) as a robust and versatile nanocatalyst was synthesized and well-characterized by using Fourier transform infrared (FT-IR), transmission electron microscopy (TEM), scanning electron microscopy (SEM), energy dispersive X-ray (EDX), X-ray mapping, thermogravimetric analysis (TGA), differential thermal analysis (DTA), Brunauer–Emmett–Teller (BET), X-ray diffraction (XRD), and inductively coupled plasma optical emission spectroscopy (ICP-OES). The synthesis of 5-substituted 1H-tetrazoles and the oxidation of sulfides were conducted by BNPs@Cur-Ni with excellent turnover number (TON) and turnover frequency (TOF) outcomes. Also, the catalyst was reused for several sequential runs without Ni leaching or decreasing in reaction yield. Utilizing the curcumin and boehmite with a natural source as well as poly(ethylene glycol) (PEG) as a solvent in this simple protocol can be based on green chemistry rules.
Jani, Muhammed Ali,Bahrami, Kiumars
(2020/09/21)

Fabricated copper catalyst on biochar nanoparticles for the synthesis of tetrazoles as antimicrobial agents
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
(2019/11/05)

Methionine-Coated Fe3O4 Nanoparticles: An Efficient and Reusable Nanomagnetic Catalyst for the Synthesis of 5-Substituted 1H-Tetrazoles
Abstract: Methionine-coated Fe3O4 nanoparticles, a magnetically reusable and environmentally friendly heterogeneous catalyst, was synthesized. The new catalyst was characterized by FT-IR spectra, XRD, SEM, and EDX analysis and was us
Abbasi, R.,Karimian, A.,Namvar-Mhaboub, M.
p. 1646 - 1653
(2020/10/22)

VASCULAR ADHESION PROTEIN-1 (VAP-1) MODULATORS AND THERAPEUTIC USES THEREOF
Disclosed herein are small molecule Vascular Adhesion Protein- 1 (VAP-1) modulator compositions, pharmaceutical compositions, the use and preparation thereof.
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Paragraph 0258

(2020/01/24)

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
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
(2019/08/20)

Copper(II)-faciliated synthesis of substituted thioethers and 5-substituted 1H-tetrazoles: Experimental and theoretical studies
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.
p. 194 - 206
(2019/06/24)

A Facile Approach to Catalyst-Free Cyanation and Azidation of a-Organic Compounds and a One-Pot Preparation of 5-Substituted 1 H-Tetrazoles by Using a Dimethyl Sulfoxide-Nitric Acid Combination
In this study, cyanations or azidations of imines were performed by using hydroxy(dimethyl)-λ 4-sulfanecarbonitrile or azido(dimethyl)-λ 4-sulfanol, respectively, prepared in situ by treatment of potassium cyanide or sodium azide with a dimethyl sulfoxide-nitric acid combination. Furthermore, a one-pot preparation of 5-substituted 1 H-tetrazole derivatives was carried out by using this reagent combination in the presence of an aldehyde, hydroxylamine hydrochloride, and sodium azide under mild conditions.
Alavi, Seyyedeh Ameneh,Kazemnejadi, Milad,Mahmoudi, Boshra,Nasseri, Mohammad Ali
supporting information
p. 2290 - 2294
(2019/12/11)

Humic acid as an efficient and reusable catalyst for one pot three-component green synthesis of 5-substituted 1: H -tetrazoles in water
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
p. 784 - 789
(2020/01/23)

A practical multigram-scale method for the green synthesis of 5-substituted-1H-tetrazoles in deep eutectic solvent
A series of 5-substituted-1H-tetrazoles have been efficiently synthesized in moderate to excellent yields (68–90%) under mild reaction conditions by combining aryl aldehydes, hydroxylamine hydrochloride with sodium azide in the presence of catalytic amoun
Xiong, Xingquan,Yi, Chao,Liao, Xu,Lai, Shilin
p. 402 - 406
(2019/01/05)

Tandem magnetization and post-synthetic metal ion exchange of metal–organic framework: Synthesis, characterization and catalytic study
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
(2019/03/08)

Immobilization of Pd(0) complex on the surface of SBA-15: A reusable catalyst for the synthesis of 5-substituted tetrazoles, sulfides and sulfoxides
A simple and efficient method for the synthesis of 5-substituted tetrazoles, sulfides and sulfoxides in the presence of Pd(0) complex immobilized on mesoporous SBA-15 as an efficient, recoverable and thermally stable mesostructure has been reported. Also, the prepared mesostructure was characterized by Fourier transform infrared spectroscopy, scanning electron microscopy, X-ray mapping, energy-dispersive X-ray spectroscopy, N2 adsorption and desorption, inductively coupled plasma optical emission spectroscopy and thermal gravimetric analysis. Then, this mesostructured catalyst was applied in the synthesis of 5-substituted tetrazoles, sulfides and sulfoxides. The approach described here offers advantages such as short reaction times, high yield, purity yields, simple and eco- friendly, easy work-up. More importantly, this nanohybrid robust catalyst did not undergo metal leaching and applied several times without any decrease in catalytic activity.
Tamoradi, Taiebeh,Ghorbani-Choghamarani, Arash,Ghadermazi, Mohammad
p. 374 - 380
(2018/11/01)

La complex supported on magnetic nanoparticles: green, efficient, novel and reusable nanocatalyst for the synthesis of 5-substituted tetrazoles and the oxidation reactions in neat condition
In the present work, we were interested in the synthesis of green and novel magnetic nanocatalyst by anchoring La complex on Fe3O4. The nanocatalyst was successfully synthesized and characterized by FT-IR, SEM, TGA, XRD, EDX, and ICP techniques. The designed procedure shows many benefits such as short reaction time, high yield, excellent purity, eco-friendly catalyst, easy workup and easy recovery from the reaction mixture by external magnet. [Figure not available: see fulltext.].
Tamoradi, Taiebeh,Irandoust, Asrin,Ghadermazi, Mohammad
p. 1723 - 1733
(2019/07/03)

Neodymium immobilized on Fe3O4: A new and recoverable catalyst for oxidation reactions and synthesis of 5‐substituted 1H-tetrazoles in green condition
Magnetic nanoparticle functionalized with neodymium complex as catalyst and characterized by SEM, XRD, FT-IR, TGA, EDX and ICP techniques. Then, catalytic activity of prepared catalyst was examined in the synthesis of tetrezoles and oxidation reactions in
Ghadermazi, Mohammad,Taherabadi, Samira,Tamoradi, Taiebeh
p. 305 - 311
(2019/08/12)

Ordered mesoporous SBA-15 functionalized with yttrium(III) and cerium(III) complexes: Towards active heterogeneous catalysts for oxidation of sulfides and preparation of 5-substituted 1H-tetrazoles
Mesoporous SBA-15 was synthesized and modified with 3-chloropropyltrimethoxysilane and then used in immobilization of creatinine groups, which were employed to introduce Y3+ and Ce3+ to give rise to two novel yttrium and cerium catalysts: SBA-15@Creatinine@M (M?=?Y and Ce). The structures of the SBA-15@Creatinine@M catalysts were determined using various techniques. These catalysts offered outstanding catalytic performances in the oxidation of sulfides to sulfoxides and in the preparation of 5-substituted 1H-tetrazoles. An important characteristic of the SBA-15@Creatinine@M catalysts is that they are very stable without a considerable decrease in their catalytic performance lasting seven cycles.
Molaei, Somayeh,Tamoradi, Taiebeh,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash
(2018/11/25)

Immobilization of Gd(III) complex on Fe3O4: A novel and recyclable catalyst for synthesis of tetrazole and S–S coupling
In the present work, a novel catalysts prepared by the anchoring of Gd(III) complex with OH groups on the surface of Fe3O4 in which characterized by FT-IR, TGA, XRD, EDX, VSM, and ICP-OES techniques and tested in the synthesis of tetrazoles and S–S coupling. This designed methods indicated several advantages including easily recovered from the reaction mixture by magnetic field, several consecutive cycles without noticeable change in its catalytic activity, the use of green solvent, the use of aspartic acid as green ligand, chemical and physical stability of obtained catalyst, short time reaction and good to excellent isolated yields of all product. Also, up to date, Gd(III) complex don't used for the synthesis of tetrazoles and S–S coupling.
Nemati, Mohammad,Tamoradi, Taiebeh,Veisi, Hojat
p. 75 - 84
(2019/05/06)

Immobilization of cerium (IV) and erbium (III) in mesoporous MCM-41: Two novel and highly active heterogeneous catalysts for the synthesis of 5-substituted tetrazoles, and chemo- and homoselective oxidation of sulfides
Two well-ordered 2D-hexagonal cerium (IV) and erbium (III) embedded functionalized mesoporous MCM-41(MCM-41@Serine/Ce and MCM-41@Serine/Er) have been developed via functionalization of mesoporous MCM-41. The surface modification method has been used in the preparation of serine-grafted MCM-41 and led to the development of MCM-41@Serine. The reaction of MCM-41@Serine with Ce (NH4)2(NO3)6·2H2O or ErCl3·6H2O in ethanol under reflux led to the organization of MCM-41@Serine/Ce and MCM-41@Serine/Er catalysts. The structures of these catalysts were determined using scanning electron microscopy, mapping, energy-dispersive X-ray spectroscopy, Fourier transform-infrared, thermogravimetric analysis, X-ray diffraction, inductively coupled plasma, and Brunauer–Emmett–Teller analysis. These MCM-41@Serine/Ce and MCM-41@Serine/Er catalysts show outstanding catalytic performance in sulfides oxidation and synthesis of 5-substituted tetrazoles. These catalysts can be recycled for seven repeated reaction runs without showing a considerable decrease in catalytic performance.
Molaei, Somayeh,Ghadermazi, Mohammad
(2019/05/07)

Catalytic Synthesis of 5-Substituted Tetrazoles: Unexpected Reactions and Products
Tetrazoles are incredibly useful organic molecules with a wide range of applications from medicinal chemistry as carboxylic acid isosteres to high energy density materials in space research. In an effort to develop an easy protocol for the synthesis of te
Wani, Mohmmad Y.,Silva, Manuela R.,Krishnakumar, Balu,Kumar, Santosh,Al-Bogami, Abdullah S.,Aqlan, Faisal M.,Sobral, Abilio J. F. N.
p. 1613 - 1621
(2019/04/26)

Iron (III)-porphyrin Complex FeTSPP as an efficient catalyst for synthesis of tetrazole derivatives via [2?+?3]cycloaddition reaction in aqueous medium
The metal complex (5,10,15,20-tetrakis-(4-sulfonatophenyl)-porphyrin-iron (III) chloride (FeTSPP) was new employed in an environmentally benign protocol as an efficient catalyst for a “click” chemistry approach for the synthesis of tetrazole and guanindinyltetrazole derivatives via [2?+?3] cycloaddition reaction of nitriles and azide derivatives in aqueous medium. The synthesized compounds were obtained in excellent yield, short reaction times and a recoverable catalyst.
El-Remaily, Mahmoud Abd El Aleem Ali Ali,Elhady
(2019/06/08)

Tin-Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles from Nitriles: Homogeneous and Heterogeneous Procedures
The preparation of 5-substituted 1H-tetrazoles was efficiently achieved by reaction of trimethylsilylazide with nitriles using a triorganotin alkoxide precatalyst. The reaction mechanism was first investigated using a homogeneous tributyltin derivative and was explored through experimental investigations and DFT calculations. A heterogeneous version was then developed using a polymer-supported organotin alkoxide and afforded an efficient method for the preparation of tetrazoles in high yields with an easy work-up and a residual tin concentration in the desired products compatible for pharmaceutical applications (less than 10 ppm). (Figure presented.).
Chrétien, Jean-Mathieu,Kerric, Gaelle,Zammattio, Fran?oise,Galland, Nicolas,Paris, Michael,Quintard, Jean-Paul,Le Grognec, Erwan
supporting information
p. 747 - 757
(2019/01/04)

Enhanced Thermocatalytic Activity of Porous Yellow ZnO Nanoflakes: Defect- and Morphology-Induced Perspectives
Herein, we report a simple and effective strategy for the synthesis of yellow ZnO (Y-ZnO) nanostructures with abundant oxygen vacancies on a large scale, through the sulfidation of ZnO followed by calcination. The developed strategy allows retention of the overall morphology of Y-ZnO compared with pristine ZnO and the extent of oxygen vacancies can be tuned. The influence of oxygen deficiencies, the extent of defect sites, and the morphology of ZnO on its solution-phase thermocatalytic activity has been evaluated in the synthesis of 5-substituted-1H-tetrazoles with different nitriles and sodium azide. A reasonable enhancement in the reaction rate was achieved by using Y-ZnO nanoflakes (Y-ZnO NFs) as a catalyst in place of pristine ZnO NFs. The reaction was complete within 6 h at 110 °C with Y-ZnO NFs, whereas it took 14 h at 120 °C with pristine ZnO NFs. The catalyst is easy to recycle without a significant loss in catalytic activity.
Galani, Sunil M.,Panda, Asit Baran
p. 612 - 620
(2019/02/14)

Andrographolide compounds as well as preparation method, pharmaceutical compositions and applications thereof
The present invention discloses andrographolide compounds as well as a preparation method, pharmaceutical compositions and applications thereof. The andrographolide compounds (I), isomers, prodrugs, solvates, or pharmaceutically acceptable salts thereof h
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Paragraph 0157-0159

(2018/05/16)

Facile one-pot preparation of 5-aryltetrazoles and 3-arylisoxazoles from aryl bromides
The successive treatment of aryl bromides with n-BuLi, DMF, hydroxylamine hydrochloride, and finally diphenylphosphoryl azide provided efficiently the corresponding 5-aryltetrazoles in good to moderate yields. Similarly, the successive treatment of aryl bromides with n-BuLi, DMF, hydroxylamine hydrochloride, and finally diethyl acetylenedicarboxylate and Oxone provided efficiently the corresponding diethyl 3-arylisoxazole-4,5-dicarboxylates in good to moderate yields. Aromatic aldoximes are the key intermediates in both reactions, and 5-aryltetrazoles and 3-arylisoxazoles could be obtained from aryl bromides in one pot under transition-metal-free conditions.
Kobayashi, Eiji,Togo, Hideo
p. 4226 - 4235
(2018/07/06)

Dendrimer-encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe3O4@SiO2 nanoparticles as a novel recyclable catalyst for N-arylation of nitrogen heterocycles and green synthesis of 5-substituted 1H-tetrazoles
In this study, dendrimer-encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe3O4@SiO2 nanoparticles were prepared via a multistep-synthesis. Then, the synthesized composite was fully characterized by various techniques such as fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD), dynamic light scattering (DLS), UV-vis spectroscopy, energy dispersive X-ray analysis (EDX), thermogravimetric analysis (TGA) and vibration sample magnetometer (VSM). From the information gained by. FE-SEM and TEM studies it can be inferred that the particles are mostly spherical in shape and have an average size of 50?nm. Also, the amount of Cu is determined to be 0.51?mmol/g in the catalyst by inductively coupled plasma (ICP) analyzer. This magnetic nano-compound has been successfully applied as a highly efficient, magnetically recoverable and stable catalyst for N-arylation of nitrogen heterocycles with aryl halides (I, Br) and arylboronic acids without using external ligands or additives. The catalyst was also employed in a one-pot, three-component reaction for the efficient and green synthesis of 5-substituted 1H-tetrazoles using various aldehydes, hydroxylamine hydrochloride and sodium azide in water. The magnetic catalyst can be easily separated by an external magnet bar and is recycled seven times without significant loss of its activity.
Esmaeilpour, Mohsen,Sardarian, Ali Reza,Firouzabadi, Habib
(2018/03/21)

TiCl3 catalyzed one-pot protocol for the conversion of aldehydes into 5-substituted 1H-tetrazole
An efficient protocol has been explored for the one-pot synthesis of tetrazole derivatives with wide functional group compatibility in moderate to very high yields starting from aliphatic and aromatic substituted aldehydes. The reaction proceeds via non-isolated oxime and nitrile intermediates. The structures of the products were confirmed by IR and NMR spectroscopy. A plausible reaction mechanism is also provided.
Ranjan Chakraborty, Rakesh,Ghosh, Pranab
p. 3616 - 3619
(2018/09/11)

One pot three-component synthesis of 5-substituted 1H-tetrazole from aldehyde
A versatile, robust and efficient strategy for the synthesis of vast range of highly functionalized 5-substituted 1H-tetrazole derivatives by using one pot three-component synthesis from various aldehydes, hydroxylamine hydrochloride and sodium azide in p
Mitra, Bijeta,Mukherjee, Suvodip,Pariyar, Gyan Chandra,Ghosh, Pranab
supporting information
p. 1385 - 1389
(2018/03/12)

Immobilization of a nickel complex onto functionalized Fe3O4 nanoparticles: a green and recyclable catalyst for synthesis of 5-substituted 1H-tetrazoles and oxidation reactions
Abstract: In the present research, a magnetically recoverable catalyst was easily prepared by anchoring nickel onto the surface of organically modified magnetite nanoparticles. Characterization of the prepared nanostructure was performed by various physico-chemical techniques such as Fourier transform infrared spectroscopy, scanning electron microscopy, transmission electron microscopy, energy-dispersive X-ray spectroscopy, inductively coupled plasma optical emission spectroscopy, X-ray diffraction, thermal gravimetric analysis and vibrating sample magnetometer measurements. The catalytic behavior of the prepared nanohybrid as an efficient catalyst was successfully probed in the oxidation of sulfides, oxidative coupling of thiols and synthesis of 5-substituted 1H-tetrazoles. This method was found to have significant advantages, including high yield, green reaction conditions, short reaction time, easy separation and workup, as well as the ability to tolerate a wide variety of substitutions in the reagents. Graphical Abstract: [Figure not available: see fulltext.].
Tamoradi, Taiebeh,Mehraban-Esfandiari, Bita,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash
p. 1363 - 1380
(2017/10/30)

Unprecedented formation of a μ-oxobridged polymeric copper(II) complex: Evaluation of catalytic activity in synthesis of 5-substituted 1H-tetrazoles
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.
p. 16 - 22
(2018/06/20)

Engineering a Cu-MOF Nano-Catalyst by using Post-Synthetic Modification for the Preparation of 5-Substituted 1H-Tetrazoles
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
(2018/07/31)

A new Pd-Schiff-base complex on boehmite nanoparticles: Its application in Suzuki reaction and synthesis of tetrazoles
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
(2018/04/14)

Preparation of Ag-doped g-C3N4 Nano Sheet Decorated Magnetic γ-Fe2O3@SiO2 Core–Shell Hollow Spheres through a Novel Hydrothermal Procedure: Investigation of the Catalytic activity for A3, KA2 Coupling Reactions and [3?+?2] Cycloaddition
Taking advantageous of both g-C3N4 and magnetic core-shell hollow spheres, for the first time a heterogeneous and magnetically separable hybrid system was prepared through a novel and simple hydrothermal procedure and used for immobilization of bio-synthesized Ag(0) nanoparticles. The hybrid system was fully characterized by using SEM/EDS, FTIR, VSM, TEM, XRD, TGA, DTGA, ICP-AES, BET and elemental mapping analysis. The catalytic utility of the obtained system, h-Fe2O3@SiO2/g-C3N4/Ag, for promoting ultrasonic-assisted A3, KA2 coupling reactions and [3?+?2] cycloaddition has been confirmed. The results established that the catalyst could efficiently catalyze the reaction to afford the corresponding products in high yields in short reaction times. The reusability study confirmed that the catalyst could be recovered and reused for at least five reaction runs with only slight loss of the catalytic activity. The hot filtration test also proved low silver leaching, indicating the heterogeneous nature of the catalysis.
Sadjadi, Samahe,Malmir, Masoumeh,Heravi, Majid M.
(2018/07/31)

Synthesis and crystal structures of salen-type Cu(II) and Ni(II) Schiff base complexes: application in [3+2]-cycloaddition and A3-coupling reactions
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.
p. 13754 - 13762
(2018/08/21)