- 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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- 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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- Synthesis and Characterization of Magnetic Functionalized Ni and Cu Nano Catalysts and Their Application in Oxidation, Oxidative Coupling and Various Multi-Component Reactions
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Abstract: Two magnetic nano catalysts of nickel and copper, Fe3O4@SiO2@DOP-BenPyr-M(II), (M=Ni and Cu) have been synthesized. These catalysts were applied as recoverable, efficient and new heterogeneous catalysts for the high yielding and room temperature one-pot procedure of selective oxidation of sulfides to sulfoxides and oxidative coupling of thiols to disulfides. In addition, the catalytic activity of Fe3O4@SiO2@DOP-BenPyr-Ni(II) was investigated as heterogeneous nanocatalyst for synthesis of 2,3-dihydroquinazolin-4(1H)-ones, 5-substituted 1H-tetrazoles and polyhydroquinolines. The synthesized catalysts were characterized by FT-IR, TGA, XRD, VSM, EDX, ICP and SEM techniques. These catalysts were recovered by an external magnet and reused several times without significant loss of catalytic efficiency. Graphic Abstract: [Figure not available: see fulltext.]
- Hajjami, Maryam,Sheikhaei, Shiva,Gholamian, Fatemeh,Yousofvand, Zakieh
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p. 2420 - 2435
(2021/01/04)
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- Fabricated copper catalyst on biochar nanoparticles for the synthesis of tetrazoles as antimicrobial agents
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Biochar is a carbon-rich solid which its surface was covered by high density of carbonyl, hydroxyl and carboxylic acid functional groups. In this work, biochar nanoparticles were prepared from pyrolysis of chicken manure and further a new copper catalyst
- Moradi, Parisa,Hajjami, Maryam,Tahmasbi, Bahman
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- Copper and nickel immobilized on cytosine@MCM-41: as highly efficient, reusable and organic–inorganic hybrid nanocatalysts for the homoselective synthesis of tetrazoles and pyranopyrazoles
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In this work, a green approach is reported for efficient synthesis of biologically active tetrazole and pyranopyrazole derivatives in the presence of Cu-Cytosine@MCM-41 and Ni-Cytosine@MCM-41 (copper (II) and nickel (II) catalyst on the modified MCM-41 us
- Nikoorazm, Mohsen,Tahmasbi, Bahman,Gholami, Shahab,Moradi, Parisa
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- 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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p. 1307 - 1317
(2019/11/14)
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- Palladium fabricated on boehmite as an organic-inorganic hybrid nanocatalyst for C-C cross coupling and homoselective cycloaddition reactions
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Herein, boehmite nanoparticles were prepared using an aqueous solution of NaOH and Al(NO3)3?9H2O at room temperature. After modification of the boehmite nanoparticle (BNP) surface by 3-choloropropyltrimtoxysilane (CPTMS), adenine was anchored on the surface. Finally, a complex of palladium was fabricated on the BNP surface (Pd-adenine@boehmite). The obtained nanoparticles were identified by TGA, FT-IR, BET, EDS, WDX, SEM, XRD and AAS techniques. In continuation, the Pd-adenine@boehmite was employed as an efficient, reusable and organic-inorganic hybrid catalyst in the C-C cross coupling reactions without a phosphine ligand or an inert atmosphere. Moreover, the homoselective synthesis of tetrazoles was studied in the presence of Pd-adenine@boehmite as a heterogeneous and practical nanocatalyst which can be recovered and reused in the described organic reactions. Besides, organic products which were isolated in suitable TOF and TON numbers in the presence of Pd-adenine@boehmite as a catalyst revealed the practicality of this catalyst. The heterogeneous nature of this catalyst was confirmed by TEM, EDS, WDX, AAS, and FT-IR techniques and, then, compared to the fresh catalyst.
- Tahmasbi, Bahman,Ghorbani-Choghamarani, Arash,Moradi, Parisa
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p. 3717 - 3727
(2020/03/17)
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- Copper-based catalysts derived from salen-type ligands: Synthesis of 5-substituted-1: H-tetrazoles via [3+2] cycloaddition and propargylamines via A3-coupling reactions
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Base-metal copper(ii) complexes derived from unsymmetrical salen-type ligands were designed and synthesized using ligands L1H to L4H in moderate yield. The synthesized unsymmetrical ligands L1H to L4H and the corresponding copper complexes (1-4) were characterized by UV-visible, IR and ESI-MS spectroscopic studies. Molecular structures of complexes 1, 2 and 4 were determined by X-ray crystallography. Copper complexes 1-4 were employed as catalysts for [3+2] cycloaddition and A3-coupling reactions. The mutual approach of salen-type ligands and metals via active participation of ligands allow to achieve the catalytic reactions. Reaction pathways were proposed and possible intermediate species during the catalytic cycle were successfully characterized by ESI-MS spectroscopic studies. This journal is
- Singh, Anshu,Maji, Ankur,Mohanty, Aurobinda,Ghosh, Kaushik
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p. 18399 - 18418
(2020/11/13)
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- Boehmite@SiO2@ Tris (hydroxymethyl)aminomethane-Cu(I): a novel, highly efficient and reusable nanocatalyst for the C-C bond formation and the synthesis of 5-substituted 1H-tetrazoles in green media
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In this work, a versatile protocol was introduced for the preparation of a new Cu(I) supported complex on Silica supported boehmite nanoparticles (Boehmite@SiO2@Tris-Cu(I)). The structure of the catalyst was comprehensively characterized using
- Ghorbani-Choghamarani, Arash,Aghavandi, Hamid,Mohammadi, Masoud
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- 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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- 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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- 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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- 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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- 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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- 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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- 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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- Cationic organotin cluster [t-Bu2Sn(OH)(H2O)]2 2+2OTf?-catalyzed one-pot three-component syntheses of 5-substituted 1H-tetrazoles and 2,4,6-triarylpyridines in water
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The cationic organotin cluster [t-Bu2Sn(OH)(H2O)]2 2+2OTf? is easy to prepare and stable in air. The catalytic activity of [t-Bu2Sn(OH)(H2O)]2 2+2OTf? as a neutral organotin Lewis acid catalyst is probed through the one-pot three-component syntheses of 5-substituted 1H-tetrazoles from aldehydes, hydroxylamine hydrochloride and sodium azide, and of 2,4,6-triarylpyridines from aromatic aldehydes, substituted acetophenones and ammonium acetate. The reactions proceed well in the presence of 1?mol% of [t-Bu2Sn(OH)(H2O)]2 2+2OTf? in water and provide the corresponding 5-substituted 1H-tetrazoles and 2,4,6-triarylpyridines in good to excellent yields. The method reported has several advantages such as the catalyst being neutral, low catalyst loading and use of water as a green solvent.
- Wang, Hongshe,Zhao, Weixing,Du, Juan,Wei, Fenyan,Chen, Qi,Wang, Xiaomei
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- Humic acid as an efficient and reusable catalyst for one pot three-component green synthesis of 5-substituted 1: H -tetrazoles in water
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Humic acid is a non toxic, inexpensive, easily available high-molecular weight polymer. A simple and facile one pot three-component synthesis of 5-substituted 1H-tetrazoles from aldehydes, hydroxyamine hydrochloride and sodium azide using humic acid as an efficient catalyst in water is described. The method reported has several advantages such as high to excellent yields, easy work-up, mild reaction conditions, use of water as a green solvent, and a commercially available, nontoxic and reusable catalyst.
- Wang, Hongshe,Wang, Yichun,Han, Yinfeng,Zhao, Weixing,Wang, Xiaomei
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p. 784 - 789
(2020/01/23)
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- Anchoring Ni (II) on Fe3O4@tryptophan: A recyclable, green and extremely efficient magnetic nanocatalyst for one-pot synthesis of 5-substituted 1H-tetrazoles and chemoselective oxidation of sulfides and thiols
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A green, novel and extremely efficient nanocatalyst was successfully synthesized by the immobilization of Ni as a transition metal on Fe3O4 nanoparticles coated with tryptophan. This nanostructured material was characterized using Fourier transform infrared spectroscopy, transmission electron microscopy, scanning electron microscopy, energy-dispersive X-ray spectroscopy, thermogravimetric analysis, inductively coupled plasma optical emission spectroscopy, vibrating sample magnetometry and X-ray diffraction. The prepared nanocatalyst was applied for the oxidation of sulfides, oxidative coupling of thiols and synthesis of 5-substituted 1H-tetrazoles. The use of non-toxic, green and inexpensive materials, easy separation of magnetic nanoparticles from a reaction mixture using a magnetic field, efficient and one-pot synthesis, and high yields of products are the most important advantages of this nanocatalyst.
- Moeini, Nazanin,Tamoradi, Taiebeh,Ghadermazi, Mohammad,Ghorbani-Choghamarani, Arash
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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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- 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
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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.
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- Facile one-pot preparation of 5-aryltetrazoles and 3-arylisoxazoles from aryl bromides
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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
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p. 4226 - 4235
(2018/07/06)
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- Development and Demonstration of a Safer Protocol for the Synthesis of 5-Aryltetrazoles from Aryl Nitriles
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The search for a faster, safer protocol for the direct synthesis of 5-aryltetrazoles from aryl nitriles in the presence of sodium azide and an amine hydrochloride salt led to the discovery of a buffered system comprised of BnNH2, BnNH2·HCl, and NaN3. After optimization of reaction conditions and a thorough investigation of reaction safety, the procedure was demonstrated for the synthesis of several hundred grams of 4-chloro-2-(2H-tetrazol-5-yl)phenol. The generality of the developed reaction conditions was established by a small-scale reactivity screen using 16 additional aryl and heteroaryl nitrile substrates.
- Treitler, Daniel S.,Leung, Simon,Lindrud, Mark
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p. 460 - 467
(2017/03/24)
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- Anchoring of Cu(II)–vanillin Schiff base complex on MCM-41: A highly efficient and recyclable catalyst for synthesis of sulfides and 5-substituted 1H–tetrazoles and oxidation of sulfides to sulfoxides
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A copper(II)–vanillin complex was immobilized onto MCM-41 nanostructure and was used as an inexpensive, non-toxic and heterogeneous catalyst in the synthesis of symmetric aryl sulfides by the cross-coupling of aromatic halides with S8 as an effective sulfur source, in the oxidation of sulfides to sulfoxides using 30% H2O2 as a green oxidant and in the synthesis of 5-substituted 1H–tetrazoles from a smooth (3?+?2) cycloaddition of organic nitriles with sodium azide (NaN3). The products were obtained in good to excellent yields. This catalyst could be reused several times without loss of activity. Characterization of the catalyst was performed using Fourier transform infrared, energy-dispersive X-ray and atomic absorption spectroscopies, X-ray diffraction, thermogravimetric analysis, and scanning and transmission electron microscopies.
- Khanmoradi, Maryam,Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash
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- Cu(II) immobilized on Fe3O4@APTMS-DFX nanoparticles: An efficient catalyst for the synthesis of 5-substituted 1: H -tetrazoles with cytotoxic activity
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Cu(ii) immobilized on deferasirox loaded amine functionalized magnetic nanoparticles (Cu(ii)/Fe3O4@APTMS-DFX) as a novel magnetically recyclable heterogeneous catalyst is able to catalyze the [3 + 2] cycloaddition reactions of various organic nitriles with sodium azide. Using this method, a series of 5-substituted-1H-tetrazoles under mild conditions in DMSO were prepared. The reaction involves mild reaction conditions with efficient transformation capability. The developed catalyst could be easily separated by applying an external magnetic field. Furthermore, it could be recycled for 5 runs with negligible leaching of copper from the surface of the catalyst. The catalyst was characterized by various techniques such as FT-IR, TGA, VSM, SEM-EDX, and ICP-OES. Several derivatives of 1H-tetrazoles were prepared using this catalyst, and their structures were confirmed using different techniques. Then, the synthesized anthraquinones were evaluated for their cytotoxicity against several cell lines including MCF-7, MAD-MD-231, HT-29, HeLa, neuro-2a and L-929. The results obtained from the MTT assay revealed that the 6 derivatives exhibited a high level of cytotoxicity. In order to determine the cytotoxicity mechanism, 2 derivatives with the highest cytotoxic activity were selected, and an apoptosis assay was carried out by flow cytometry, which supported that apoptosis is the major mechanism.
- Taghavi, Faezeh,Gholizadeh, Mostafa,Saljooghi, Amir Sh.,Ramezani, Mohammad
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p. 1953 - 1964
(2017/10/27)
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- First report of the direct supporting of palladium–arginine complex on boehmite nanoparticles and application in the synthesis of 5-substituted tetrazoles
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Boehmite nanoparticles are aluminium oxide hydroxide (γ-AlOOH) particles, which were prepared using a simple and inexpensive procedure in water at room temperature and further modified using arginine. Subsequently palladium particles were immobilized on their surface to prepare Pd-Arg@boehmite. This novel nanostructured compound was fully characterized using thermogravimetric analysis, X-ray diffraction, inductively coupled plasma optical emission (ICP-OES) and energy-dispersive X-ray spectroscopies, and scanning and transmission electron microscopies. Finally, this catalyst was applied as a moisture- and air-stable heterogeneous material for the synthesis of 5-substituted 1H–tetrazole derivatives. The leaching of palladium and heterogeneity of the catalyst were studied using hot filtration and ICP-OES. This catalyst demonstrated remarkable recyclability. The novelty of this work is that it represents the first time an amino acid has been grafted on boehmite nanoparticles.
- Tahmasbi, Bahman,Ghorbani-Choghamarani, Arash
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- High Catalytic Activity of Peptide Nanofibres Decorated with Ni and Cu Nanoparticles for the Synthesis of 5-Substituted 1H-Tetrazoles and N-Arylation of Amines
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A rapid development of a new methodology for decarboxylative N-arylation of carboxylic acids and the preparation of 5-substituted 1H-tetrazoles catalysed by peptide nanofibres decorated with Cu and Ni nanoparticles is presented. Compared with conventional aryl halides, benzoic acids are extremely interesting and environmentally friendly options for the synthesis of secondary aryl amines.
- Ghorbani-Choghamarani, Arash,Taherinia, Zahra
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p. 1127 - 1137
(2017/10/10)
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- Diisopropylethylammonium acetate (DIPEAc): An efficient and recyclable catalyst for the rapid synthesis of 5-substituted-1H-tetrazoles
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A simple and efficient protocol developed for the synthesis of 5-substituted 1H-tetrazole derivatives through [2+3] cycloaddition reaction between benzonitriles and sodium azide using diisopropylethylammonium acetate as a recyclable reaction medium is described. The reactions proceed well at 80 °C and provide the corresponding tetrazoles in good to excellent yields (up to 94% yield). Developed method has notable advantages, such as simple and mild conditions, easy workup, reusability with consistent catalytic activity, and safer alternative to hazardous, corrosive conventional Lewis acid catalysts.
- Bhosle, Manisha R.,Shaikh, Dastgir S.,Khillare, Lalit D.,Deshmukh, Amarsinh R.,Mane, Ramrao A.
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supporting information
p. 695 - 703
(2017/03/27)
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- Pd-SBT@MCM-41: As an efficient, stable and recyclable organometallic catalyst for C-C coupling reactions and synthesis of 5-substituted tetrazoles
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A palladium S-benzylisothiourea complex was anchored on functionalized MCM-41 (Pd-SBT@MCM-41) and applied as efficient and reusable catalyst for the synthesis of 5-substituted 1H–tetrazoles using [2?+?3] cycloaddition reaction of various organic nitriles with sodium azide (NaN3) in poly(ethylene glycol) (PEG) as green solvent. Also this catalyst was applied as an versatile organometallic catalyst for Suzuki cross-coupling reaction of aryl halides and phenylboronic acid (PhB(OH)2) or sodium tetraphenyl borate (NaB(Ph)4). This nanocatalyst was characterized by thermal gravimetric analysis (TGA), X-ray Diffraction (XRD), scanning electron microscopy (SEM), inductively Coupled Plasma (ICP) and N2 adsorption–desorption isotherms techniques. Recovery of the catalyst is easily achieved by centrifugation for several consecutive runs.
- Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash,Ghobadi, Massoud,Massahi, Shokofeh
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- Method for preparing tetrazole compound
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The invention discloses a method for preparing a tetrazole compound. The tetrazole compound is synthesized/prepared from cyanobenzene or substituted cyanobenzene and sodium azide, which serve as raw materials, in a manner of taking dimethylformamide as a
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Paragraph 0037; 0038
(2017/08/28)
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- Triple reuptake inhibitors: Design, synthesis and structure–activity relationship of benzylpiperidine–tetrazoles
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Monoamine transporters are important targets in the treatment of various central nervous disorders. Several limitations of traditional reuptake inhibitors, like delayed onset of action, insomnia, and sexual dysfunction, have compelled the search for safer, more effective compounds. In this study, we have sought to identify novel monoamine reuptake inhibitors. Based upon the docking study of compounds that we had reported previously, aromatic rings (A1) were modified to generate a novel series of benzylpiperidine–tetrazoles. Thirty-one compounds were synthesized and evaluated for their triple reuptake inhibition of serotonin, norepinephrine and dopamine. Triple reuptake inhibitor, compound 2q, in particular, showed potent serotonin reuptake inhibition, validating our design approach.
- Paudel, Suresh,Min, Xiao,Acharya, Srijan,Khadka, Daulat Bikram,Yoon, Goo,Kim, Kyeong-Man,Cheon, Seung Hoon
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p. 5278 - 5289
(2017/10/06)
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- [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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p. 7365 - 7374
(2017/09/06)
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- Efficient synthesis of 5-substituted tetrazoles catalysed by palladium–S-methylisothiourea complex supported on boehmite nanoparticles
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An efficient and general method is reported for the synthesis of 5-substituted 1H-tetrazole derivatives in the presence of S-methylisothiourea complex of palladium immobilized on boehmite nanoparticles (Pd-SMTU@boehmite) as an efficient and recyclable nan
- Moradi, Parisa,Ghorbani-Choghamarani, Arash
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- Synthesis of 5-substituted 1H-tetrazoles from aryl halides using nanopolymer-anchored palladium(II) complex as a new heterogeneous and reusable catalyst
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Abstract: This paper reports on the preparation and use of chloromethylated polystyrene-anchored palladium(II) complex, [Ps-ttet-Pd(II)], as a separable nanocatalyst for the synthesis of 5-substituted 1H-tetrazoles by treating aryl halides with K4[Fe(CN)6] as non-toxic cyanide source, to generate in situ the corresponding aryl nitriles which then react through [2?+?3] cycloaddition with sodium azide. High yields of the products, simple methodology, easy work-up procedure, high catalytic activity, and superior cycling stability of the catalyst are the main advantages of this protocol. The structure of the catalyst was characterized using the powder XRD, SEM, TG-DTA, EDS, AAS, and FT-IR spectroscopy techniques. Graphical abstract: [Figure not available: see fulltext.]
- Tajbakhsh, Mahmood,Alinezhad, Heshmatollah,Nasrollahzadeh, Mahmoud,Kamali, Taghi A.
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p. 2135 - 2142
(2016/11/17)
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- Ni-S-methylisothiourea complexes supported on boehmite nanoparticles and their application in the synthesis of 5-substituted tetrazoles
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Boehmite nanoparticles are aluminum oxide hydroxide (γ-AlOOH) particles, which were prepared by a simple and inexpensive procedure and immobilized further with nickel-S-methylisothiourea complexes (Ni-SMTU@boehmite), and characterized by FT-IR spectroscopy, TGA, XRD, ICP-OES, EDS, SEM and TEM techniques. Finally, we investigated the catalytic activity of Ni-SMTU@boehmite as a new, heterogeneous, stable and highly reusable nanocatalyst for the synthesis of 5-substituted 1H-tetrazole derivatives in PEG-400 as a green solvent. This catalyst was recovered by simple filtration and reused several times without significant loss of its catalytic efficiency or nickel leaching. The heterogeneity of this catalyst has been studied using hot filtration and ICP-OES technique.
- Ghorbani-Choghamarani, Arash,Moradi, Parisa,Tahmasbi, Bahman
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p. 56638 - 56646
(2016/07/06)
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- Application of Pd-2A3HP-MCM-41 to the Suzuki, Heck and Stille coupling reactions and synthesis of 5-substituted 1H-tetrazoles
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An ecofriendly heterogeneous catalyst has been synthesized by anchoring palladium onto the surface of organically modified mesoporous silica. The prepared catalyst was characterized using X-ray diffraction, Fourier transform infrared and energy-dispersive X-ray spectroscopies, transmission and scanning electron microscopies, inductively coupled plasma and thermogravimetric techniques. The catalyst shows high activity in the Suzuki, Heck and Stille cross-coupling reactions and the synthesis of 5-substituted 1H-tetrazoles from sodium azide (NaN3). These methods have the advantages of high yields, green reaction conditions, simple methodology and easy separation and workup.
- Nikoorazm, Mohsen,Ghorbani-Choghamarani, Arash,Khanmoradi, Maryam
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p. 705 - 712
(2016/07/19)
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- The first report on the eco-friendly synthesis of 5-substituted 1: H -tetrazoles in PEG catalyzed by Cu(ii) immobilized on Fe3O4@SiO2@l-arginine as a novel, recyclable and non-corrosive catalyst
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Cu(ii) immobilized on Fe3O4@SiO2@l-aginine as a novel, inexpensive and non-corrosive nanostructured compound catalyzed the cycloaddition reaction of various organic nitriles with sodium azide. This combination leads to obt
- Ghorbani-Choghamarani, Arash,Shiri, Lotfi,Azadi, Gouhar
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p. 32653 - 32660
(2016/05/09)
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- Piperazinium dihydrogen sulfate: An acidic ionic liquid for the [3+2] cycloaddition reaction of sodium azide with organic nitriles
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Background: Tetrazoles are imperative nitrogen rich heterocyclic compounds with a wide range of applications in the field of organic synthesis, coordination chemistry, material sciences, and medicinal chemistry. A most common approach for the synthesis of 5-substituted-1H-Tetrazoles is achieved by [3+2] cycloaddition reaction of azides to nitriles. In this paper a new acidic ionic liquid is introduced as a catalyst to promote the mentioned reaction. Methods: Piperazinium dihydrogen sulfate:as a new acidic ionic compound was obtained by treatment of piperazine with sulfuric acid, which is further was applied as a catalyst for the [3+2] cycloaddition reaction of azides to organic nitriles. Results: The [3+2] cycloaddition reaction of sodium azide with structurally different organic nitriles using only 1.5 mol% of the piperazinium dihydrogen sulfate proceeded well at 100°C and 5-substituted-1H-Tetrazoles were prepared in good to excellent yields. Herein, piperazinium dihydrogen sulfate has a dual role of catalyst and reaction medium, which circumvents the use of any organic solvent. The catalyst is also recyclable. This method is particularly suitable for benzonitriles carrying deactivating groups which furnished the corresponding products in excellent yields. By this method, mono [3+2] cycloaddition product of dicyanides was obtained. Conclusion: In conclusion, piperazinium dihydrogen sulfate as a new acidic ionic compound was applied to promote synthesis of 5-substituted-1H-Tetrazoles through [3+2] cycloaddition reaction of organic nitriles with sodium azide. This new ionic compound can be easily separated from the reaction mixture which resulted to a simple work-up of the products.
- Nowrouzi, Najmeh,Farahi, Soghra,Irajzadeh, Maryam
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p. 113 - 119
(2016/02/27)
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- Cu-MCM-41 nanoparticles: An efficient catalyst for the synthesis of 5-substituted 1H-tetrazoles via [3+2] cycloaddition reaction of nitriles and sodium azide
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[3 + 2] cycloaddition reaction of various types of nitriles and sodium azide (NaN 3) were studied in the presence of nano-sized Cu-MCM-41 as an efficient recoverable heterogeneous catalyst. Nano-sized Cu-MCM-41 mesoporous molecular sieves with various Si/Cu molar ratios were synthesized by direct insertion of metal ions at room temperature. The textural properties of the materials have been studied by means of XRD, FTIR, SEM and TEM techniques. Catalytic behavior of Cu-MCM-41 was also investigated by pyridine absorption and potentiometric titration. The reactions data verified characterization results and show that Cu-MCM-41 with Si/Cu molar ratio of 20 has considerably better catalytic activity compared to the other molar ratios. To investigate reusability, the catalyst was recovered by simple filtration and reused for several cycles with consistent activity.
- Abdollahi-Alibeik, Mohammad,Moaddeli, Ali
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- Activated Fuller's earth as an inexpensive, eco-friendly, efficient catalyst for the synthesis of 5-aryl 1-H-tetrazole via [3+2] cycloaddition of nitriles and sodium azide
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A simple and efficient method for the preparation of 5-aryl 1-H-tetrazoles was developed from various aryl nitriles and sodium azide (NaN3) via [3+2] cycloaddition reaction using activated Fuller's earth as an efficient heterogeneous catalyst.
- Rekunge, Deelip S.,Indalkar, Krishna S.,Chaturbhuj, Ganesh U.
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supporting information
p. 5815 - 5819
(2016/12/06)
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- Ag-doped nano magnetic γ-Fe2O3@DA core-shell hollow spheres: An efficient and recoverable heterogeneous catalyst for A3 and KA2 coupling reactions and [3 + 2] cycloaddition
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An effective protocol for the fabrication of Ag-doped nano magnetic γ-Fe2O3@DA core-shell hollow spheres (h-Fe2O3@DA/Ag) by a simple hydrothermal method is demonstrated without any templates in the reaction system. The synthesized core-shell structure was successfully characterized in terms of the chemical composition, surface morphology, and magnetic properties using FT-IR, VSM, TGA, TEM, FE-SEM, EDS, and XRD patterns. The possible formation mechanism of this magnetic γ-Fe2O3@DA/Ag hollow sphere structure is described based on the experimental results. In addition, as a physical property, the apparent shell density was determined using the specific surface area (BET) and shell thickness (BJH). The important, novel and unique catalyst with a hollow structural character and strong magnetic behavior exhibited a high catalytic activity in the A3 and KA2 coupling reactions and [3 + 2] cycloaddition for the synthesis of 1H-tetrazoles. Furthermore, the recovered catalyst of the reaction mixture was facilitated by a magnetic field and multiple recycling was carried out without any significant loss in the catalytic activity.
- Elhampour,Malmir,Kowsari,Boorboor Ajdari,Nemati
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p. 96623 - 96634
(2016/10/25)
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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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p. 739 - 742
(2015/01/30)
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- Multi-component one-pot reaction of aldehyde, hydroxylamine and sodium azide catalyzed by Cu-MCM-41 nanoparticles: A novel method for the synthesis of 5-substituted 1H-tetrazole derivatives
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A simple and efficient procedure for the synthesis of 5-substituted 1H-tetrazole derivatives has been developed using a one-pot, three-component reaction of various aldehydes, hydroxylamine and sodium azide in the presence of a catalytic amount of Cu-MCM-41, as a nanostructured, heterogeneous and reusable catalyst. In this research, Cu-MCM-41 nanoparticles with three Cu/Si molar ratios were prepared and characterized using various techniques. The characterization and optimization results show that the catalyst with a Cu/Si molar ratio of 0.050 has the best catalytic activity.
- Abdollahi-Alibeik, Mohammad,Moaddeli, Ali
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p. 2116 - 2122
(2015/03/18)
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- Green synthesis of 5-substituted-1H-1,2,3,4-tetrazoles and 1-sustituted-1H-1,2,3,4-tetrazoles via [3+2] cycloaddition by reusable immobilized AlCl3on -Al2O3
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We report the effectiveness of the surface modified γ-Al2O3which is reusable, efficient, catalytic, safe and environmentally acceptable procedure for the conversion of both alkyl and aryl nitriles into the corresponding 5-substituted-1H-1,2,3,4-tetrazoles via [3+2] cycloaddition with sodium azide in excellent yields at mild reaction conditions (50 ° C). The catalyst also afforded 1-substituted-1H-1,2,3,4-tetrazoles by the reaction of amines, sodium azide and triethyl orthoformate. The catalyst could be recycled and was reused eleven runs without losing its activity.
- Nanjundaswamy, Hemmaragala Marishetty,Abrahamse, Heidi
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p. 2137 - 2150
(2015/01/09)
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- Nano TiO2/SO42- as a heterogeneous solid acid catalyst for the synthesis of 5-substited-1 H-tetrazoles
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An efficient and economical protocol for the synthesis of 5-substituted-1H-tetrazoles from various nitriles and sodium azide is reported using nano TiO2/SO42+ as an effective heterogeneous catalyst.A wide variety of aryl nitriles underwent [3 + 2] cycloaddition to afford tetrazoles in good to excellent yields.
- Hosseini-Sarvari, Mona,Najafvand-Derikvandi, Sepideh
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p. 1007 - 1012
(2015/01/09)
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- Synthesis, characterization and catalytic activity of graphene oxide/ZnO nanocomposites
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This paper reports on the synthesis and use of graphene oxide/ZnO nanocomposite as a heterogeneous catalyst for the synthesis of various tetrazoles. The catalyst was characterized by X-ray diffraction (XRD), scanning electron microscopy (SEM), energy dispersive X-ray spectroscopy (EDS), transmission electron microscopy (TEM) and UV-vis spectroscopy. This method has the advantages of high yields, elimination of homogeneous catalysts or corrosive acids, simple methodology and easy work up. Another important factor is the stability and recyclability of the catalyst under the reaction conditions used. This heterogeneous catalyst shows no significant loss of activity in the recycling experiments. the Partner Organisations 2014.
- Nasrollahzadeh, Mahmoud,Jaleh, Babak,Jabbari, Ameneh
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p. 36713 - 36720
(2014/12/09)
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- Organocatalysis by an aprotic imidazolium zwitterion: A dramatic anion-cation cooperative effect on azide-nitrile cycloaddition
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An aprotic imidazole based zwitterionic-salt, 4-(3-methylimidazolium)butane sulfonate (MBS) has been found to be an efficient organocatalyst for the synthesis of 5-substituted 1H-tetrazoles by the cycloaddition of aryl nitriles with NaN3 under solvent-free conditions. Both the cation and the anion cooperatively affect the reaction and the C2-H of the imidazolium moiety plays a crucial role in "electrophilic activation" of the nitrile through hydrogen bond formation.
- Rahman, Matiur,Roy, Anupam,Ghosh, Monoranjan,Mitra, Shubhanjan,Majee, Adinath,Hajra, Alakananda
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p. 6116 - 6119
(2014/01/23)
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