- Fe3O4/ZnS hollow nanospheres: A highly efficient magnetic heterogeneous catalyst for synthesis of 5-substituted 1H-tetrazoles from nitriles and sodium azide
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An efficient route for the synthesis of 5-substituted 1H-tetrazole via [2+3] cycloaddition of nitriles and sodium azide is reported using Fe 3O4/ZnS hollow nanospheres as a magnetic separable heterogeneous catalyst. The catalyst is very efficient, affording excellent yields and can be reused for several circles. In addition, the Fe 3O4 inner shell exhibits magnetism, making the catalyst easily separated by a magnet. The catalyst can be easily separated by a magnet for further reuse. After reused for three times, the catalytic activity can maintain 90% of the initial value and exhibits good magnetism. Copyright
- Qi, Gang,Liu, Wei,Bei, Zhining
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- 4-(N,N-Dimethylamino)pyridinium acetate as a recyclable catalyst for the synthesis of 5-substituted-1H-tetrazoles
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An efficient method for the synthesis of 5-substituted-1H-tetrazoles through the reaction of nitriles with sodium azide using 4-(N,N-dimethylamino)pyridinium acetate as a recyclable catalyst with ionic liquid character is described. The reactions proceed well at 100 °C and provide the corresponding tetrazoles in good to excellent yields. This method has the advantage of easy work-up of the product without the requirement of HCl. Mono [3+2] cycloaddition products were obtained from dicyanides via this method.
- Nowrouzi, Najmeh,Farahi, Soghra,Irajzadeh, Maryam
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- Mesoporous AlPO4: A highly efficient heterogeneous catalyst for synthesis of 5-substituted 1H-tetrazoles from nitriles and sodium azide via [3 + 2] cycloaddition
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The mesoporous AlPO4 with high surface area and fine mesoporous structure was prepared by a soft template method and showed excellent catalytic performance for synthesis of 5-substituted 1H-tetrazoles from various nitriles and sodium azide with
- Ai, Man,Lang, Leiming,Li, Baojun,Xu, Zheng
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- Enhanced Thermocatalytic Activity of Porous Yellow ZnO Nanoflakes: Defect- and Morphology-Induced Perspectives
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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
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- [Cu(phen)(PPh3)2]NO3-catalyzed microwave-assisted green synthesis of 5-substituted 1H-tetrazoles
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Abstract: An efficient synthetic methodology for construction of 5-substituted 1H-tetrazoles under microwave irradiation in green medium is described. With [Cu(phen)(PPh3)2]NO3 as catalyst and H2O-isopropyl alcohol (IPA) as reaction medium, various substituted nitriles underwent (3?+?2) cycloaddition reaction with NaN3 under microwave irradiation to provide corresponding 5-substituted 1H-tetrazoles in high yield. This method is not only efficient and general but also benefits from high functional group tolerance. This environmentally friendly synthetic methodology is visualized as an alternative to existing procedures, providing a simple route to privileged scaffolds.
- Padmaja,Meena,Maiti, Barnali,Chanda, Kaushik
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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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- A robust and recyclable ionic liquid-supported copper(II) catalyst for the synthesis of 5-substituted-1H-tetrazoles using microwave irradiation
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Abstract: A novel and robust ionic liquid-supported copper(II) catalyst has been developed and explored for the efficient synthesis of 5-substituted-1H-tetrazoles using microwave irradiation. The ionic liquid-supported catalyst facilitated the efficient isolation of tetrazole products with high purity by simple extraction with organic solvent. Recovered ionic liquid-supported copper(II) catalyst could be recycled for three times for the synthesis of tetrazole products with high purity. This synthetic protocol offers a very clean, convenient, and microwave-assisted environment-friendly method for the efficient synthesis of 5-substituted-1H-tetrazoles with high yield. Graphic abstract: [Figure not available: see fulltext.].
- Padmaja,Chanda, Kaushik
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- γ-Fe2O3: A magnetic separable catalyst for synthesis of 5-substituted 1H-tetrazoles from nitriles and sodium azide
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An efficient route for the synthesis of 5-substituted 1H-tetrazole via [2+3] cycloaddition of nitriles and sodium azide is reported using γ-Fe2O3 nanoparticles as a magnetic separable catalyst. Under optimized conditions, the moderate to good yields (71-95%) can be obtained. The catalyst can be easily separated by a magnet and reused for several circles.
- Qi, Gang,Dai, Yong
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- 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
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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
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- 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
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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
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- The mineral alum: an effective and low-cost heterogeneous catalyst for the successful synthesis of 5-substituted-1H-tetrazoles
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A simple, efficient, and green procedure for the synthesis of 5-substituted-1H-tetrazoles via [3 + 2] cycloaddition reaction of nitriles with sodium azide is described. The reaction was catalyzed by natural and mesoporous alum nanoparticles (NPs) in DMSO
- Karimian, Azam,Emarloo, Nahid,Salari, Samira
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- An efficient Cu/functionalized graphene oxide catalyst for synthesis of 5-substituted 1H-tetrazoles
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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.
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p. 2891 - 2899
(2021/02/12)
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- Practical scale up synthesis of carboxylic acids and their bioisosteres 5-substituted-1H-tetrazoles catalyzed by a graphene oxide-based solid acid carbocatalyst
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Herein, catalytic application of a metal-free sulfonic acid functionalized reduced graphene oxide (SA-rGO) material is reported for the synthesis of both carboxylic acids and their bioisosteres, 5-substituted-1H-tetrazoles. SA-rGO as a catalytic material incorporates the intriguing properties of graphene oxide material with additional benefits of highly acidic sites due to sulfonic acid groups. The oxidation of aldehydes to carboxylic acids could be efficiently achieved using H2O2as a green oxidant with high TOF values (9.06-9.89 h?1). The 5-substituted-1H-tetrazoles could also be effectively synthesized with high TOF values (12.08-16.96 h?1). The synthesis of 5-substituted-1H-tetrazoles was corroborated by single crystal X-ray analysis and computational calculations of the proposed reaction mechanism which correlated well with experimental findings. Both of the reactions could be performed efficiently at gram scale (10 g) using the SA-rGO catalyst. SA-rGO displays eminent reusability up to eight runs without significant decrease in its productivity. Thus, these features make SA-rGO riveting from an industrial perspective.
- Mittal, Rupali,Kumar, Amit,Awasthi, Satish Kumar
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p. 11166 - 11176
(2021/03/31)
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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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- 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
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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
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- 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
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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
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- Polymer-Supported Fe-Phthalocyanine Derived Heterogeneous Photo-Catalyst for the Synthesis of Tetrazoles Under Visible Light Irradiation
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Abstract: Herein, a polymer supported Fe-Phthalocyanine entangled with carboxyl functionalized benzimidazolium moiety (PSFePcCFBM) explored as heterogenous photocatalyst, for regioselective synthesis of 1H-tetrazoles from sodium azide and other affordable
- Khajone, Vijay Baburao,Balinge, Kamlesh Rudreshwar,Bhagat, Pundlik Rambhau
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p. 1948 - 1960
(2020/11/23)
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- 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
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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
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p. 19203 - 19220
(2021/06/03)
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- Magnetic nitrogen-doped carbon derived from silk cocoon biomass: a promising and sustainable support for copper
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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
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- Methionine-Coated Fe3O4 Nanoparticles: An Efficient and Reusable Nanomagnetic Catalyst for the Synthesis of 5-Substituted 1H-Tetrazoles
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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.
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p. 1646 - 1653
(2020/10/22)
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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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- 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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- Copper coordinated-poly(α-amino acid) decorated on magnetite graphene oxide as an efficient heterogeneous magnetically recoverable catalyst for the selective synthesis of 5- and 1-substituted tetrazoles from various sources: A comparative study
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In this work, poly(α-amino acid)-Cu(II) complex immobilized on magnetite graphene oxide (GO/Fe3O4?PAA-Cu-complex) was prepared via a multistep synthesis and employed as an efficient, heterogeneous, magnetically recyclable nanocatalyst for one-pot, three component synthesis of 5- and 1-substituted tetrazoles using different substrates including benzaldehydes, benzonitriles, and anilines in mild conditions. The different approaches were mechanically investigated and compared. The catalyst was fully characterized by Fourier transform infrared (FTIR), thermogravimetric analysis (TGA), X-ray diffraction (XRD), vibrating sample magnetometer (VSM), energy dispersive X-ray spectroscopy (EDX), inductively coupled plasma (ICP), FE-SEM and TEM analyses. The magnetic nanocatalyst could be readily separated from the reaction mixture by an external magnet and reused for several times without significant loss of catalytic activity. Also, the spectroscopic analysis revealed the stability and durability of the catalyst. Finally, the chemoselectivity of the method was investigated by the various combinations of aldehyde, nitrile, and oxime.
- Kazemnejadi, Milad,Mahmoudi, Boshra,Sharafi, Zeinab,Nasseri, Mohammad A.,Allahresani, Ali,Esmaeilpour, Mohsen
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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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- 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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- Anchoring of Cu (II)-Schiff base complex on magnetic mesoporous silica nanoparticles: catalytic efficacy in one-pot synthesis of 5-substituted-1H-tetrazoles, antibacterial activity evaluation and immobilization of α-amylase
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Magnetic mesoporous silica nanocomposite, Fe3O4?MCM-41, was prepared and functionalized with N-(2-aminoethyl)-3-aminopropyltrimethoxysilane (AEAPS). Then Schiff base grafted nanoparticles were synthesized by the condensation of 5,5'-
- Ahmadi, Ameneh,Azadi, Roya,Motamedi, Hossein,Sedaghat, Tahereh
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- Highly active and reusable cu/c catalyst for synthesis of 5-substituted 1h-tetrazoles starting from aromatic aldehydes
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A new, efficient and convenient method for the synthesis of 5-substituted 1H-tetrazole derivatives with a wide range of substituents in good to excellent yields has been developed. The synthesis was performed by the one-pot three-component [3+2]cycloaddit
- Khalifeh, Reza,Khalili, Dariush,Rastegar, Najme
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p. 1044 - 1052
(2021/06/07)
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- Catalytic Synthesis of 5-Substituted Tetrazoles: Unexpected Reactions and Products
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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.
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p. 1613 - 1621
(2019/04/26)
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- 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
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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
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- 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
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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
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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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- Iron (III)-porphyrin Complex FeTSPP as an efficient catalyst for synthesis of tetrazole derivatives via [2?+?3]cycloaddition reaction in aqueous medium
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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
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- Synthesis of α-Aminonitriles and 5-Substituted 1H-Tetrazoles Using an Efficient Nanocatalyst of Fe3O4@SiO2–APTES-supported Trifluoroacetic Acid
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Fe3O4@SiO2–APTES-supported trifluoroacetic acid nanocatalyst was used for the one-pot synthesis of α-aminonitriles via a three-component reaction of aldehydes (or ketones), amines, and sodium cyanide. This method produced a high yield of 75–96% using only a small amount of the catalyst (0.05?g) in EtOH at room temperature. The catalyst was also employed for the synthesis of 5-substituted 1H-tetrazoles from nitriles and sodium azide in EtOH at 80°C. The tetrazoles were produced with good-to-excellent yields in a short reaction time of 4?h. Both synthetic methods were carried out in the absence of an organic volatile solvent. Because the supported trifluoroacetic acid generated a solid acid on the surface, thus the acid corrosiveness was not a serious challenge. This heterogeneous nanocatalyst was magnetically recovered and reused several times without significant loss of catalytic activity.
- Fatahi, Hosna,Jafarzadeh, Mohammad,Pourmanouchehri, Zahra
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p. 2090 - 2098
(2019/07/05)
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- Immobilization of Gd(III) complex on Fe3O4: A novel and recyclable catalyst for synthesis of tetrazole and S–S coupling
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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
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- Tin-Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles from Nitriles: Homogeneous and Heterogeneous Procedures
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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
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supporting information
p. 747 - 757
(2019/01/04)
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- 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
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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
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p. 1723 - 1733
(2019/07/03)
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- Immobilization of Pd(0) complex on the surface of SBA-15: A reusable catalyst for the synthesis of 5-substituted tetrazoles, sulfides and sulfoxides
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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
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p. 374 - 380
(2018/11/01)
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- Neodymium immobilized on Fe3O4: A new and recoverable catalyst for oxidation reactions and synthesis of 5‐substituted 1H-tetrazoles in green condition
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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
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p. 305 - 311
(2019/08/12)
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- Impregnated copper ferrite on mesoporous graphitic carbon nitride: An efficient and reusable catalyst for promoting ligand-free click synthesis of diverse 1,2,3-triazoles and tetrazoles
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Magnetic CuFe2O4/g-C3N4 hybrids were synthesized through a facile method and their catalytic performances were evaluated in click chemistry for the first time. The structural and morphological characterization of prepared materials was carried out by different techniques such as X-ray diffraction, high-resolution transmission electron microscopy, field emission scanning electron microscopy, Fourier infrared spectroscopy, vibrating sample magnetometry, thermogravimetric analysis, and N2 adsorption–desorption analysis (Brunauer–Emmett–Teller surface area). The utilization of magnetic CuFe2O4/g-C3N4 enabled superior performance in the one-pot azide–alkyne cycloaddition reaction in water using alkyl halides and epoxides as azide precursors without the need of any additional agents. The present system is broad in scope and especially practical for the synthesis of macrocyclic triazoles and also tetrazoles. In addition, the catalytic system highly fulfills the demands of “green click chemistry” with its convenient conditions, especially easy access to a variety of significant products in low catalyst loading and simple work-up and isolation procedure.
- Khalili, Dariush,Rezaee, Meysam
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- Biosynthesis of Pd/MnO2 nanocomposite using Solanum melongena plant extract and its application for the one-pot synthesis of 5-substituted 1H-tetrazoles from aryl halides
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In this work, for the first time, Solanum melongena plant extract was used for the green synthesis of Pd/MnO2 nanocomposite via reduction osf Pd(II) ions to Pd(0) and their immobilization on the surface of manganese dioxide (MnO2) nanoparticles (NPs) as an effective support. The synthesized nanocomposite were characterized by various analytical techniques such as Fourier transform infrared (FT-IR), X-ray diffraction (XRD), transmission electron microscopy (TEM), field emission scanning electron microscopy (FESEM), energy dispersive X-ray spectroscopy (EDS) and UV–Vis spectroscopy. The catalytic activity of Pd/MnO2 nanocomposite was used as a heterogeneous catalyst for the one-pot synthesis of 5-substituted 1H-tetrazoles from aryl halides containing various electron-donating or electron-withdrawing groups in the presence of K4[Fe (CN)6] as non-toxic cyanide source and sodium azide. The products were obtained in good yields via a simple methodology and easy work-up. The nanocatalyst can be recycled and reused several times with no remarkable loss of activity.
- Nasrollahzadeh, Mahmoud,Ghorbannezhad, Fatemeh,Sajadi, S. Mohammad
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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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- 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
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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
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supporting information
p. 2290 - 2294
(2019/12/11)
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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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- 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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- A practical multigram-scale method for the green synthesis of 5-substituted-1H-tetrazoles in deep eutectic solvent
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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
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p. 402 - 406
(2019/01/05)
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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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- PYRIDINE BASED IONIC FLUORIDE FOR CATALYZING INDOLE AND TETRAZOLE FORMATION
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A pyridine based ionic liquid with a fluoride counter anion which catalyzes Fischer indole reaction and click chemistry. Methods of preparing the ionic liquid, and methods of utilizing the ionic liquid as a catalyst to synthesize indoles/indolenines and tetrazoles are also provided.
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Paragraph 0033; 0034; 0124-0126; 0128
(2020/01/02)
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- [3 + 2] Cycloaddition promoted by zinc oxide nanoparticles anchored on reduced graphene oxide using green solvent
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ZnO anchored on RGO-catalyzed [3 + 2] cycloaddition of nitriles and sodium azide in the synthesis of 5-substituted 1H-tetrazoles in water is an efficient and simple protocol with low catalyst loading under reflux condition. It is applied to a wide range of substrates with an excellent yield, simple workup procedure, recovery, and reusability of catalyst with consistent activity and high turnover number. It is proposed that the functional groups present in RGO surface are effective for preventing the aggregation of catalytically active ZnO species during the reaction. Moreover, the excellent performance of ZnO–RGO nanocomposite is ascribed to the excellent dispersity of catalyst in water, hydrophilic nature of the RGO for the accumulation of organic substrates in water, and the “Breslow effect.”.
- Clarina, Thanaraj,Rama, Velladurai
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supporting information
p. 175 - 187
(2018/01/01)
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- Immobilization of a nickel complex onto functionalized Fe3O4 nanoparticles: a green and recyclable catalyst for synthesis of 5-substituted 1H-tetrazoles and oxidation reactions
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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
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p. 1363 - 1380
(2017/10/30)
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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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- L -Proline: An Efficient Organocatalyst for the Synthesis of 5-Substituted 1 H -Tetrazoles via [3+2] Cycloaddition of Nitriles and Sodium Azide
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A simple and efficient route for the synthesis of a series of 5-substituted 1 H -tetrazoles using l -proline as a catalyst from structurally diverse organic nitriles and sodium azide is reported. The prominent features of this environmentally benign, cost effective, and high-yielding l -proline-catalyzed protocol includes simple experimental procedure, short reaction time, simple workup, and excellent yields making it a safer and economical alternative to hazardous Lewis acid catalyzed methods. The protocol was successfully applied to a broad range of substrates, including aliphatic and aryl nitriles, organic thiocyanates, and cyanamides.
- Bhagat, Saket B.,Telvekar, Vikas N.
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supporting information
p. 874 - 879
(2018/02/16)
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- In silico identification, synthesis and biological evaluation of novel tetrazole inhibitors of MurB
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In the context of antibacterial drug discovery resurgence, novel therapeutic targets and new compounds with alternative mechanisms of action are of paramount importance. We focused on UDP-N-acetylenolpyruvylglucosamine reductase (i.e. MurB), an underexplo
- Hrast, Martina,Juki?, Marko,Patin, Delphine,Tod, Julie,Dowson, Christopher G.,Roper, David I.,Barreteau, Hélène,Gobec, Stanislav
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p. 1101 - 1112
(2018/02/19)
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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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- 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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