- Tetrazoles: A new class of compound for crystallization modification
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Tetrazoles are a class of organic compound often used as carboxylic acid analogues. This analogous behaviour is shown to extend to crystallization modification, that is, tetrazoles are also able to influence crystal growth and morphology although in a dif
- Massi, Massimiliano,Ogden, Mark I.,Radomirovic, Tomoko,Jones, Franca
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- A three-dimensional highly stable Zn(II) coordination polymer based on 1,4-benzeneditetrazolate (H2BDT): Synthesis, crystal structure, and luminescent properties
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1,4-benzeneditetrazolate [H2BDT] (1) and its 3D coordination polymer [Zn(BDT)]n (2), have been synthesized and structurally characterized by infrared spectroscopy (IR), thermal gravimetric analysis (TG), and single-crystal/powder X-r
- Deng, Ji-Hua,Yuan, Xiao-Lin,Mei, Guang-Quan
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- CuO–NiO bimetallic nanoparticles supported on graphitic carbon nitride with enhanced catalytic performance for the synthesis of 1,2,3-triazoles, bis-1,2,3-triazoles, and tetrazoles in parts per million level
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The unification of CuCl2·2H2O and NiCl2·6H2O with the support of graphitic carbon nitride yielded to form an efficient, synergistic, bimetallic nano-catalyst CuO–NiO@g-C3N4. FT-IR, SEM, TEM
- Gajurel, Sushmita,Dam, Binoyargha,Bhushan, Mayank,Singh, L. Robindro,Pal, Amarta Kumar
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- Dendron-functionalized Fe3O4 magnetic nanoparticles with palladium catalyzed CN insertion of arylhalide for the synthesis of tetrazoles and benzamide
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A novel method for the one-pot synthesis of 5-substituted 1H-tetrazoles and Benzamide from arylhalide containing in situ CN insertion from inorganic salt source was accomplished in presence of a new magnetically catalyst, palladium on surface-modified Schiff-Base complex. K2[Ni(CN)4] plays a role of nontoxic inorganic cyanide source in arylhalide Nucleophilic substitution. The synthesized Pd-Schiff-Base@Fe3O4MNPs was characterized by various techniques such as FT-IR, TGA, SEM, VSM, XRD, TEM, ICP-AES, EDX, BET and XPS. The nano structure catalyst was easily recovered by external magnetic field and reused several times without noticeable loss of its catalytic activity. Leaching study of Pd-Schiff-Base@Fe3O4 MNPs shows palladium strong bonded to different active parts of catalyst surface. Heterogeneity of this catalyst has been examined using hot filtration and ICP-AES techniques.
- Karimi Zarchi, Mohammad Ali,Darbandizadeh Mohammad Abadi, Seyed Shahab Addin
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p. 196 - 212
(2018/11/24)
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- Tandem magnetization and post-synthetic metal ion exchange of metal–organic framework: Synthesis, characterization and catalytic study
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For the first time, metal-exchange in a magnetic metal–organic framework (MOF) via tandem magnetization and post-synthetic modification has been developed. The new magnetic mixed-metal metal–organic framework nanocomposite, CoFe2O4/[
- Yadollahi, Mahtab,Hamadi, Hosein,Nobakht, Valiollah
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- Synthesis, Biological Activity, and Molecular Docking Assessment of Some New Sulfonylated Tetrazole Derivatives
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The designed molecular structures have been subjected to computational analysis for calculating their physicochemical properties and drug likeness. The calculated data indicate that most of the compound possess the bioactivity score in the active zone. Synthetic approach to the target compounds is straightforward and easy to handle. Structures of the new compounds are supported by FT-IR, 1H, and 13C NMR, and mass spectra. Antimicrobial tests of the products against pathogens (S. aureus, S. epidermidis, E. coli, and P. mirabilis) indicate the products as active or highly active. Their cyto-toxicity is determined to be 92–98% at concentration of 3.125 μmol/L. The molecular docking analysis carried out for the target compounds against the receptor Glc-N-6P exhibits low binding energy and various binding sites of those.
- Arshad,Khan,Nami
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p. 1851 - 1858
(2019/11/02)
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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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- A Practical Synthesis of 5-Substituted 1 H -Tetrazoles from Aldoximes Employing the Azide Anion from Diphenyl Phosphorazidate
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5-Substituted 1 H -tetrazoles were effectively synthesized from aldoximes and diphenyl phosphorazidate (DPPA) under reflux conditions in xylenes. Various aldoximes underwent the cycloaddition reaction to afford the corresponding 5-substituted 1 H -tetrazoles in short reaction times and in good yields. Chiral aldoximes derived from amino acids also gave aminotetrazoles with almost no racemization.
- Ishihara, Kotaro,Kawashima, Mayumi,Matsumoto, Takatoshi,Shioiri, Takayuki,Matsugi, Masato
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p. 1293 - 1300
(2017/12/26)
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- The self-assembly and metal adatom coordination of a linear bis-tetrazole ligand on Ag(111)
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We employ a linear linker molecule consisting of a benzene functionalised with two tetrazole moieties at para positions. Its self-assembly and coordination with the native silver adatoms and codeposited Fe adatoms on a Ag(111) surface under ultra high vacuum conditions are investigated by means of scanning tunnelling microscopy and X-ray photoelectron spectroscopy. We discover a rich spectrum of room-temperature stable Ag and Fe2+ coordination nodes depending on the formation temperature.
- Knecht, Peter,Suryadevara, Nithin,Zhang, Bodong,Reichert, Joachim,Ruben, Mario,Barth, Johannes V.,Klyatskaya, Svetlana,Papageorgiou, Anthoula C.
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supporting information
p. 10072 - 10075
(2018/09/13)
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- Utilization of ultrasonic irradiation as green and effective one-pot protocol to prepare a novel series of bis-2-amino-1, 3, 4-oxa(thia)diazoles and bis-tetrazoles
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In an effective and straightforward conversion, bis-semicarbazones and bis-thiosemicarbazones are transformed into a diversity of novel substituted bis-2-amino-1, 3, 4-oxadiazoles and bis-2-amino-1, 3, 4-thiadiazoles, respectively under ultrasonic irradiation. Bis-tetrazoles are obtained from the dialdehydes by sequential reaction with hydroxylamine hydrochloride, phosphorus pentoxide and sodium azide without isolation of the intermediates oximes and nitriles. All the reactions proceed cleanly and smoothly under mild conditions, with short reaction times and broad functional groups possibility. No side reactions were observed.
- Arafa, Wael Abdelgayed Ahmed,Abdel-Magied, Ahmed Fawzy
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p. 327 - 340
(2017/12/06)
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- A novel route for the synthesis of 5-substituted 1-: H tetrazoles in the presence of polymer-supported palladium nanoparticles
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A novel method for the synthesis of 5-substituted 1-H tetrazoles has been developed using one-pot tandem reactions of aryl halides with K4[Fe(CN)6] and sodium azide in the presence of cross-linked poly(4-vinylpyridine)-stabilized Pd(0) nanoparticles, [P4-VP]-PdNPs. The catalyst was characterized using various techniques such as FT-IR and UV-vis spectroscopy, AAS, TEM, FESEM, EDX analysis, XRD and XPS. The results confirm a good dispersion of palladium nanoparticles on the polymer support. The catalyst is reusable many times without a significant loss in its activity.
- Darbandizadeh Mohammad Abadi, Seyed Shahab Addin,Karimi Zarchi, Mohammad Ali
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supporting information
p. 10397 - 10406
(2017/09/18)
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- Antimicrobial evaluation of 5-substituted aryl 1H-tetrazoles
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Background: Tetrazole derivatives such as 1-substituted dinitrobenzyl tetrazoles and their oxa and selanyl analogs have previously been studied against drug-susceptible and multidrugresistant mycobacteria. In addition, other tetrazole derivatives have bee
- Feinn, Liana,Dudley, Joshua,Coca, Adiel,Roberts, Elizabeth L.
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p. 359 - 364
(2017/06/20)
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- Fabrication of palladium nanoparticles as effective catalysts by using supramolecular gels
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Two-component supramolecular gels were made through self-assembly of tetrazolyl derivatives and Pd(OAc)2. The robust gels indicated high storage modulus (>10,000 Pa) and loss modulus, which were studied by rheological measurements. The formed P
- Zhang, Wei,Xie, Zhi-Gang
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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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- Preparation of 5-substituted 1H-tetrazoles catalyzed by scandium triflate in water
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Several 5-substituted 1H-tetrazoles were prepared in water or isopropanol/water mixtures using microwave heating. Good yields were obtained for the [2 + 3] cycloaddition of sodium azide with aryl nitriles, aliphatic nitriles, and vinyl nitriles when catal
- Coca, Adiel,Turek, Evan,Feinn, Liana
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p. 218 - 225
(2015/11/02)
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- Microwave Synthesis of 5-Substituted 1 H-Tetrazoles Catalyzed by Bismuth Chloride in Water
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(Chemical Equation Presented). Bismuth chloride was used to catalyze the [2 + 3] cycloaddition between sodium azide with aryl nitriles, aliphatic nitriles, and vinyl nitriles. A number of 5-substituted 1H-tetrazoles were synthesized in water or isopropano
- Coca, Adiel,Feinn, Liana,Dudley, Joshua
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p. 1023 - 1030
(2015/03/30)
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- Efficient transformation of inactive nitriles into 5-substituted 1 H-tetrazoles using microwave irradiation and their applications
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Efficient transformations of inactive nitriles into 5-substituted 1H-tetrazoles in DMF in a microwave reactor are described. The present method is applied to the synthesis of tetrazolato-bridged dinuclear platinum(II) complex and tetrazole C1-ribonucleoside phosphoramidite. Georg Thieme Verlag Stuttgart, New York.
- Yoneyama, Hiroki,Usami, Yoshihide,Komeda, Seiji,Harusawa, Shinya
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p. 1051 - 1059
(2013/05/09)
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- Click chemistry for the synthesis of 5-substituted 1H-tetrazoles from boron-azides and nitriles
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A novel and metal free catalysis of synthesizing 5-substituted 1H-tetrazoles through 1,3-dipolar cycloaddition of boron-azides and nitriles is reported with broad substrate scope and excellent yields.
- Yao, Yue-Wei,Zhou, Yi,Lin, Bao-Ping,Yao, Cheng
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supporting information
p. 6779 - 6781
(2013/11/19)
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- Coordination polymer gel derived from a tetrazole ligand and Zn 2+: Spectroscopic and mechanical properties of an amorphous coordination polymer gel
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A tetrazole-based ligand forms a supramolecular gel in the presence of transition metal ions, particularly Zn2+, Cu2+ and Co 2+. The gels have been characterized by SEM, TEM, fluorescence spectroscopy, rheometry and fluore
- Lee, Hyejin,Kang, Sunwoo,Lee, Jin Yong,Jung, Jong Hwa
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experimental part
p. 2950 - 2955
(2012/05/20)
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- Iodine-catalyzed, efficient, one-pot protocol for the conversion of araldehydes into 5-aryl-1H-tetrazoles
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An easy access to various 5-aryl-1H-tetrazoles by a one-pot direct conversion of aldehydes to tetrazoles without the isolation of the intermediate nitriles using commercially available iodine as a catalyst is described. The protocol offers advantages in terms of good yields, mild reaction conditions, short reaction times, and use of readily available environmentally compatible catalyst. Copyright
- Reddy, M.B.Madhusudana,Pasha
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experimental part
p. 2081 - 2085
(2011/07/07)
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- Amine salt-catalyzed synthesis of 5-substituted 1H-tetrazoles from nitriles
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The [3+2] cycloaddition reaction between sodium azide and various organic nitriles proceeds smoothly in the presence of amine salts as catalyst in dimethylformamide. The corresponding 5-substituted 1-H tetrazoles were obtained under mild condition in good to excellent yields. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Taylor & Francis Group, LLC.
- Zhou, Yi,Yao, Cheng,Ni, Renjie,Yang, Gaowen
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experimental part
p. 2624 - 2632
(2010/10/03)
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- Antimony trioxide as an efficient Lewis acid catalyst for the synthesis of 5-substituted 1H-tetrazoles
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Sb2O3 was found to be effective as a catalyst for a smooth (2 + 3) cycloaddition of sodium azide with nitriles to afford 5-substituted 1H-tetrazoles in good yields. Copyright Taylor & Francis Group, LLC.
- Venkateshwarlu,Rajanna,Saiprakash
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experimental part
p. 426 - 432
(2009/05/30)
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- Kinetics of azidation of isomeric benzenedicarbonitriles
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Rate constants and activation parameters of two-step azidation of isomeric dicyanobenzenes with dimethylammonium azide in DMF at 70-100°C were determined. Tetrazole rings are formed from cyano groups in dicyanobenzenes in a stepwise mode following the 1,3
- Popova,Pavlyukova,Popov,Ostrovskii,Trifonov
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experimental part
p. 890 - 894
(2009/12/26)
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- Facile preparation of polytopic azoles: Synthesis, characterization, and X-ray powder diffraction studies of 1,4-bis(pyrazol-4-yl) and 1,4-bis(tetrazol-5-yl)benzene
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Two polytopic azoles, 1,4-bis(pyrazol-4-yl)benzene and 1,4-bis(tetrazol-5- yl)benzene, were prepared in sizable amounts by high yield syntheses employing, in mild conditions, cheap reactants and, whenever possible, aqueous solutions. The two species were
- Maspero, Angelo,Galli, Simona,Masciocchi, Norberto,Palmisano, Giovanni
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supporting information; experimental part
p. 956 - 957
(2009/04/05)
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- Polynuclear nonfused tetrazole-, 1,3,4-oxadiazole-, and 1,2,3-triazole-containing systems
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Polynuclear nonfused blocks containing 1,2,3-triazole, 1,3,4-oxadiazole, and tetrazole rings were synthesized by reaction of C-substituted tetrazoles with carboxylic acid chlorides, as well as by cycloaddition of 2-azidomethyl-1,3,4-oxadiazoles at the triple bond of acetylenic compounds. Pleiades Publishing, Inc., 2006.
- Vereshchagin,Petrov,Proidakov,Pokatilov,Smirnov,Kizhnyaev
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p. 912 - 917
(2007/10/03)
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- Reactions of bis(tetrazole)phenylenes. Surprising formation of vinyl compounds from alkyl halides
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The reactions of 1,2-bis(tetrazol-5-yl)benzene (1), 1,3-bis(tetrazol-5-yl) benzene (2), 1,4-bis(tetrazol-5-yl)benzene (3), 1,2-(Bu3SnN 4C)2C6H4 (4), 1,3-(Bu 3SnN4C)2C
- Fleming, Adrienne,Kelleher, Fintan,Mahon, Mary F.,McGinley, John,Prajapati, Vipa
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p. 7002 - 7011
(2007/10/03)
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- Reactions of organotin tetrazoles: Synthesis of functionalised poly-tetrazoles
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Reaction of 1,2-bis[2-(tributylstannyl)tetrazol-5-yl]benzene with 1,2-dibromoethane (1:10) yields the 1-N,1-N′-ethylene bridged cyclophane (1) while similar reactions with larger excesses (1:25) of 1,n-dibromoalkanes yield 1,2-bis[2-(bromoalkyl)tetrazol-5
- Bethel, Paul A.,Hill, Michael S.,Mahon, Mary F.,Molloy, Kieran C.
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p. 3507 - 3514
(2007/10/03)
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