- Synthesis of 5-Substituted 1 H-Tetrazoles from Nitriles by Continuous Flow: Application to the Synthesis of Valsartan
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An efficient continuous flow process for the synthesis of 5-substituted 1H-tetrazoles is described. The process involves the reaction between a polymer-supported triorganotin azide and organic nitriles. The polymer-supported organotin azide, which is in situ generated with a polystyrene-supported triorganotin alkoxide and trimethylsilylazide, is immobilized in a packed bed reactor. This approach is simple, fast (it takes from 7.5 to 15 min), and guarantees a low concentration of tin residues in the products (5 ppm). The process was developed to aryl-, heteroaryl-, and also alkylnitriles and was applied for the synthesis of valsartan, an angiotensin II receptor antagonist.
- Carpentier, Florian,Felpin, Fran?ois-Xavier,Zammattio, Fran?oise,Le Grognec, Erwan
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p. 752 - 761
(2020/03/13)
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- Synthesis and Photochemical Properties of Manganese(I) Tricarbonyl Diimine Complexes Bound to Tetrazolato Ligands
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Ten manganese(I) tricarbonyl diimine complexes bound to variably functionalised 5-aryl-tetrazolato ligands were prepared, and their photochemical properties were investigated. Upon exposure to light at 365 nm, each complex decomposed to its free diimine and tetrazolato ligands, simultaneously dissociating three CO ligands, as evidenced by changes in the IR spectra of the irradiated complexes over time. The anti-bacterial properties of one of these complexes were tested against Escherichia coli. While the complex displayed no effect on the bacterial growth in the dark, pre-irradiated solutions inhibited bacterial growth. Comparative studies revealed that the antibacterial properties originate from the presence of free 1,10-phenanthroline.
- Stout, Matthew J.,Stefan, Alessandra,Skelton, Brian W.,Sobolev, Alexandre N.,Massi, Massimiliano,Hochkoeppler, Alejandro,Stagni, Stefano,Simpson, Peter V.
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supporting information
p. 292 - 298
(2020/01/25)
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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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- Enantiomerism, diastereomerism and thermochromism in two Cu7I4 cluster-based coordination polymers
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Solvothermal reaction between CuI and 5-(3-pyridyl)tetrazole (HPTA) in CH3CN and NH3·H2O/n-BuOH, afforded two kinds of Cu7I4 cluster-based coordination polymers 1 and 2, respectively. 1 is a racemic conglomerate of enantiomers crystallizing in the P6322 space group and 2 is a mesomer crystallizing in the P3c1 group. Both 1 and 2 show dual-channel emissions in which low-energy emission originates from a cluster-centered (CC) excited state while high-energy emission is attributed to an iodide-to-ligand charge transfer (XLCT)/metal-to-ligand charge transfer (MLCT) excited state. Of particular interest, 2 exhibits thermochromic luminescence originating from the combined effects of non-radiative transition and thermal deactivation of the XLCT excited state.
- Liao, Wei-Ming,Li, Xiang-Nan,Zeng, Qi,Zhong, Yuan-Hui,Yin, Ye-Gao,He, Jun
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supporting information
p. 15136 - 15140
(2019/12/25)
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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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- Discovery, synthesis and characterization of a series of (1-alkyl-3-methyl-1H-pyrazol-5-yl)-2-(5-aryl-2H-tetrazol-2-yl)acetamides as novel GIRK1/2 potassium channel activators
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The present study describes the discovery and characterization of a series of 5-aryl-2H-tetrazol-3-ylacetamides as G protein-gated inwardly-rectifying potassium (GIRK) channels activators. Working from an initial hit discovered during a high-throughput screening campaign, we identified a tetrazole scaffold that shifts away from the previously reported urea-based scaffolds while remaining effective GIRK1/2 channel activators. In addition, we evaluated the compounds in Tier 1 DMPK assays and have identified a (3-methyl-1H-pyrazol-1-yl)tetrahydrothiophene-1,1-dioxide head group that imparts interesting and unexpected microsomal stability compared to previously-reported pyrazole head groups.
- Sharma, Swagat,Kozek, Krystian A.,Abney, Kristopher K.,Kumar, Sushil,Gautam, Nagsen,Alnouti, Yazen,David Weaver,Hopkins, Corey R.
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p. 791 - 796
(2019/02/06)
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- Syntheses and characterization of dinuclear and tetranuclear AgI supramolecular complexes generated from symmetric and asymmetric molecular clips containing oxadiazole rings
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A new asymmetric ligand, 5-{3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]phenyl}-2-(pyridin-3-yl)-1,3,4-oxadiazole (L5), which contains two oxadiazole rings, was synthesized and characterized. The assembly of symmetric 2,5-bis(pyridin-3-yl)-1,3,4-oxadiazole (L1) and asymmetric L5 with AgCO2CF3 in solution yielded two novel AgI complexes, namely catena-poly[[di-μ-trifluoroacetato-disilver(I)]-bis[μ-2,5-bis(pyridin-3-yl)-1,3,4-oxadiazole]], [Ag2(C2F3O2)2(C12H8N4O)2]n or [Ag2(μ2-O2CCF3)2(L1)2]n (1), and bis(μ3-5-{3-[5-(4-methylphenyl)-1,3,4-oxadiazol-2-yl]phenyl}-2-(pyridin-3-yl)-1,3,4-oxadiazole)tetra-μ3-trifluoroacetato-tetrasilver( I) dichloromethane monosolvate, [Ag4(C2F3O2)4(C22H15N5O2)2]μCH2Cl2 or [Ag2(μ3-O2CCF3)2(L5)]2μCH2Cl2 (2). Complex 1 displays a one-dimensional ring-chain motif, where dinuclear Ag2(CF3CO2)2 units alternate with Ag2(L1)2 macrocycles. This structure is different from previously reported Ag-L1 complexes with different anions. Complex 2 features a tetranuclear supramolecular macrocycle, in which each ligand adopts a tridentate coordination mode with the oxadiazole ring next to the p-tolyl ring coordinated and that next to the pyridyl ring free. Two L5 ligands are bound to two Ag1 centres through two oxadiazole N and two pyridyl N atoms to form a macrocycle. The other two oxadiazole N atoms coordinate to the two Ag2 centres of the Ag2(O2CCF3)4 dimer. Each CF3CO2 - anion adopts a μ3-coordination mode, bridging the Ag1 and Ag2 centres to form a tetranuclear silver(I) complex. This study indicates that the donor ability of the bridging oxadiazole rings can be tuned by electronwithdrawing and-donating substituents. The emission properties of ligands L1 and L5 and complexes 1 and 2 were also investigated in the solid state.
- Jin, Guoxia,Ji, Yuqi,Wang, Teng,Sun, Yanyan,Li, Yulong,Zhu, Guiying,Ma, Jianping
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p. 1327 - 1335
(2019/10/19)
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- Synthesis, molecular docking and xanthine oxidase inhibitory activity of 5-aryl-1H-tetrazoles
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5-Aryl-1H-tetrazoles (1–24) were synthesized and screened for their xanthine oxidase (XO) inhibitory activity using allopurinol as standard inhibitor (IC50 = 2.0 ± 0.01 μM). Six compounds 3, 4, 5, 9, 21, and 24 exhibited significant to weak act
- Fatima, Itrat,Zafar, Humaira,Khan, Khalid Mohammed,Saad, Syed Muhammad,Javaid, Sumaira,Perveen, Shahnaz,Choudhary, M. Iqbal
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p. 201 - 211
(2018/05/24)
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- A comparative study between heterogeneous stannous chloride loaded silica nanoparticles and a homogeneous stannous chloride catalyst in the synthesis of 5-substituted 1: H -tetrazole
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Heterogeneous SnCl2-nano-SiO2 efficiently catalyzed 5-substituted 1H-tetrazole synthesis with excellent yield. The catalyst was characterized by using FT-IR, TGA, TEM, and EDX. It is widely applicable on aliphatic, aromatic, heteroaromatic and sterically hindered nitriles with five time recyclability. Being simple and an economically viable approach for the synthesis of SnCl2-nano-SiO2 are additional advantages.
- Kumar, Arvind,Kumar, Satyanand,Khajuria, Yugal,Awasthi, Satish Kumar
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p. 75227 - 75233
(2016/08/24)
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- 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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- One-pot synthesis of 1- and 5-substituted 1H-tetrazoles using 1,4-dihydroxyanthraquinone–copper(II) supported on superparamagnetic Fe3O4@SiO2 magnetic porous nanospheres as a recyclable catalyst
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An effective one-pot, convenient process for the synthesis of 1- and 5-substituted 1H-tetrazoles from nitriles and amines is described using1,4-dihydroxyanthraquinone–copper(II) supported on Fe3O4@SiO2 magnetic porous nanospheres as a novel recyclable catalyst. The application of this catalyst allows the synthesis of a variety of tetrazoles in good to excellent yields. The preparation of the magnetic nanocatalyst with core–shell structure is presented by using nano-Fe3O4 as the core, tetraethoxysilane as the silica source and poly(vinyl alcohol) as the surfactant, and then Fe3O4@SiO2 was coated with 1,4-dihydroxyanthraquinone–copper(II) nanoparticles. The new catalyst was characterized using Fourier transform infrared spectroscopy, X-ray diffraction, transmission electron microscopy, field emission scanning electron microscopy, dynamic light scattering, thermogravimetric analysis, vibration sample magnetometry, X-ray photoelectron spectroscopy, nitrogen adsorption–desorption isotherm analysis and inductively coupled plasma analysis. This new procedure offers several advantages such as short reaction times, excellent yields, operational simplicity, practicability and applicability to various substrates and absence of any tedious workup or purification. In addition, the excellent catalytic performance, thermal stability and separation of the catalyst make it a good heterogeneous system and a useful alternative to other heterogeneous catalysts. Also, the catalyst could be magnetically separated and reused six times without significant loss of catalytic activity. Copyright
- Esmaeilpour, Mohsen,Javidi, Jaber,Zahmatkesh, Saeed
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p. 897 - 904
(2016/10/18)
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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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- Indium(III) Chloride Catalyzed Synthesis of 5-Substituted 1 H -Tetrazoles from Oximes and Sodium Azide
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A simple and efficient protocol has been developed for the synthesis of 5-substituted 1H-tetrazole derivatives in good to excellent yields from various oximes and sodium azide by using indium(III) chloride as a Lewis acid catalyst. The present method has
- Guggilapu, Sravanthi Devi,Prajapti, Santosh Kumar,Nagarsenkar, Atulya,Gupta, Keshav Kumar,Babu, Bathini Nagendra
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p. 1241 - 1244
(2016/05/10)
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- Synthesis of 5-substituted 1H-tetrazoles using a recyclable heterogeneous nanonickel ferrite catalyst
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An efficient method was developed for the [2 + 3] cycloaddition of sodium azide with nitriles to afford 5-substituted 1H-tetrazoles using nanonickel ferrite (NiFe2O4) as an effective heterogeneous catalyst in dimethylformamide. The main advantages of this method are high yields, simple methodology and easy work-up. The catalyst can be recovered and reused for several cycles with predictable activity.
- Abrishami, Fatemeh,Ebrahimikia, Maryam,Rafiee, Fatemeh
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p. 730 - 735
(2015/11/09)
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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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- Efficient synthesis of 5-substituted 1H-tetrazoles catalysed by silver(I) bis(trifluoromethanesulfoyl)nimide
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An efficient method is developed for the synthesis of 5-substituted 1H-tetrazoles through the [3 + 2] cycloaddition reaction of nitriles with sodium azide using silver(I) bis(trifluoromethanesulfonyl)imide (AgNTf2) as a catalyst. This procedure provides mild reaction conditions, short reaction times and high yields.
- Wang, Hongshe,Zhao, Weixing
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p. 321 - 323
(2015/08/11)
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- Application of a functionalized mesoporous silica catalyst to the synthesis of tetrazoles
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In the present study, well ordered MCM-41 was synthesized and functionalized with benzyl group and subsequently sulfonated with chlorosulfonic acid. The functionalized catalyst (MCMBSA) was characterized by XRD, TGA, FTIR, TEM, BET, and SEM. 5-Aryl-1H-tetrazoles were synthesized by the reaction of the corresponding aryl nitriles and sodium azide catalyzed by MCMBSA. The mole ratio of nitrile to sodium azide, the amount of catalyst, reaction times, and solvent type were optimized. The MCMBSA catalyst was more effective than the catalyst obtained from the direct sulfonation of MCM-41. The versatility of the method was investigated by using various nitriles, which showed reasonable yields of tetrazoles. The regeneration and reusability of catalyst was also examined.
- Najafi Chermahini, Alireza,Khani Omran, Masoud,Dabbagh, Hossein A.,Mohammadnezhad, Gholamhossein,Teimouri, Abbas
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p. 4814 - 4820
(2015/06/16)
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- Group position-dependent structurally diverse coordination compounds based on isomeric Ligands
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Two isomeric ligands Htzpya and Hpytza (Htzpya≤3-(5-tetrazolyl)pyridine-1-acetic acid, Hpytza≤5-(3-pyridyl)tetrazole-2-acetic acid) have been selected to react with DyCl3·6H2O or PrCl3·6H2O under hydrothermal conditions, resulting in the formation of four new coordination compounds, mononuclear [Dy(tzpya)2(H2O)5]Cl·4H2O (1), dinuclear [Pr2(tzpya)2(H2O)12]Cl4·2H2O (2), and two one-dimensional polymers [Dy(pytza)2Cl(H2O)2]n (3) and [Pr(pytza)2Cl(H2O)2]n (4), whose structures are controlled by the different positions of the carboxylate group. These compounds were characterized by elemental analysis, infrared spectroscopy, thermogravimetric analysis, and single-crystal X-ray diffraction. Compounds 1-4 are self-assembled to form three-dimensional network structures by hydrogen bonding interactions. Furthermore, the luminescence properties were also investigated at room temperature in the solid state.
- Zou, Jian Hua,Zhu, Jian Nan,Cui, Han Jie,Wang, Zhong,Zhu, Da Liang,Tian, He,Zhang, Fei Fei,Wang, Jing,Li, Qiao Yun,Yang, Gao Wen
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p. 889 - 895
(2015/06/25)
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- The synthesis of tetrazoles in nanometer aqueous micelles at room temperature
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A newly developed nonionic amphiphile (GPGS-1500), a diester composed of a Guerbet alcohol (2-octyldodecan-1-ol), poly(ethylene glycol) 1500 (PEG 1500), and succinic acid esters, has been prepared as an effective nanomicelle-forming species for the synthesis of tetrazoles in water at room temperature. We have designed a new nonionic amphiphile (GPGS-1500) for the synthesis of tetrazoles in water at room temperature. The reaction conditions were optimized, and the size of the micelles formed by GPGS-1500 in water was measured by dynamic light scattering. Copyright
- Xie, Aming,Cao, Meiping,Liu, Yangyang,Feng, Liandong,Hu, Xinyu,Dong, Wei
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p. 436 - 441
(2014/01/23)
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- The Synthesis of Tetrazoles in Nanometer Aqueous Micelles at Room Temperature
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A newly developed nonionic amphiphile (GPGS-1500), a diester composed of a Guerbet alcohol (2-octyldodecan-1-ol), poly(ethylene glycol) 1500 (PEG 1500), and succinic acid esters, has been prepared as an effective nanomicelle-forming species for the synthesis of tetrazoles in water at room temperature.
- Xie, Aming,Cao, Meiping,Liu, Yangyang,Feng, Liandong,Hu, Xinyu,Dong, Wei
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p. 436 - 441
(2015/10/05)
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- Facile synthesis of 1- and 5-substituted 1H-tetrazoles catalyzed by recyclable ligand complex of copper(II) supported on superparamagnetic Fe 3O4@SiO2 nanoparticles
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We report a new method for preparing functionalized superparamagnetic Fe3O4@SiO2 possessing high saturation magnetization. Magnetite particles were prepared by simple co-precipitation method in aqueous medium, and then Fe3O4@SiO2 nanosphere was synthesized by using nano Fe3O4 as the core, TEOS as the silica source and polyethylene glycol (PEG 1000) as the surfactant. Then, the silica-coated Fe3O4 nanoparticles were covered with ligand complex of Cu(II). The functionalized magnetic core-shell nanoparticles (MNPs) were investigated by Fourier transform infrared spectroscopy, transmission electron microscopy, scanning electron microscopy, X-ray diffraction, thermogravimetric analysis, dynamic light scattering and N2 adsorption/desorption. Also, its Cu content was determined by inductively coupled plasma (ICP) analyzer. Then, the immobilized copper complex was used as an efficient catalyst for synthesis of 1- and 5-substituted 1H-tetrazoles from nitriles and amines in good to excellent yields. The results show that the supported catalyst could be conveniently recovered through the use of an external magnetic field and reused for subsequent reactions for at least 6 times with less deterioration in catalytic activity.
- Esmaeilpour, Mohsen,Javidi, Jaber,Nowroozi Dodeji, Fatemeh,Mokhtari Abarghoui, Mehdi
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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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- Construction of six new coordination complexes with 5-(3-pyridyl) tetrazole-2-acetato
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Six new complexes with 3-pytza ligand (3-pytza = 5-(3-pyridyl) tetrazole-2-acetato), [Sr(3-pytza)2(H2O)2]n·nH2O (1), [Zn(3-pytza)2(H2O)2]n·2nH2O (2), [Cu(3-pytza)2(H2O)]n·2nH2O (3), [Pb(3-pytza)2]n(4), [Eu(3-pytza)2Cl(H2O)2]n(5), [Tb(3-pytza)2Cl(H2O)2]n(6) have been synthesized. These compounds were characterized by elemental analysis, IR spectroscopy and single-crystal X-ray diffraction. The X-ray analysis reveals that these compounds display 1D or 2D structures. Furthermore, the luminescent properties of 1-6 were investigated at room temperature in the solid state.
- Zou, Jian-Hua,Zhu, Da-Liang,Tian, He,Li, Fei Fei,Zhang, Fei Fei,Yang, Gao-Wen,Li, Qiao-Yun,Miao, Yun Xia
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- Microwave synthesis of mono- and bis-tetrazolato complexes via 1,3-dipolar cycloaddition of organonitriles with nickel(II)-bound azides: Isolation of 5-substituted tetrazoles from parent complex
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[2 + 3] Cycloaddition reaction of diazidonickel(II) complexes cis-[Ni(N3)2(phen)2] 1 with organonitriles NCR 2 under microwave irradiation give the bis(tetrazolato) complexes cis-[Ni(N 4CR)2(phen)2] [R = Ph (3a), 4-NC 5H4 (3b), 3-NC5H4 (3c), 4-CNPh (3d)]. Treatment of the tetrazolato complexes with excess of NaN3 liberates the free tetrazoles from the parent metal complexes. Reaction of 2-cyanopyridine with cis-[Ni(N3)2(phen)2] 1 in presence of NaClO4 gives a mono(tetrazolato) complex [Ni{5-(2-pyridyl)-tetrazolato}(phen)2](ClO4) 3e along with formation of pure 2-(1H-tetrazol-5-yl)-pyridine. Reaction of tetracyanoethylene with cis-[Ni(N3)2(bipy)2] 4 at room temperature produced a bis(tetrazolato) complex [Ni{2-cyano-3-(tetrazolato-5-yl) -but-2-enedintrile}2(bipy)2] 5. A monoazidonickel complex [Ni(N3)(H2O)(phen)2]ClO4 6 was isolated as a minor product during the synthesis of cis-[Ni(N3) 2(phen)2] 1. All the complexes obtained were characterized by IR, elemental analyses and ESI-MS apart from single crystal X-ray crystallography.
- Nasani, Rajendar,Saha, Manideepa,Mobin, Shaikh M.,Mukhopadhyay, Suman
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- The synthesis of 5-substituted 1H-tetrazoles in molten tetrabutylammonium bromide
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An economical and environmentally benign method for the synthesis of 5-substituted 1H-tetrazoles has been established. In this protocol, molten tetrabutylammonium bromide (TBAB) is used as both the solvent and catalyst. A mechanism involving the intermedi
- Xie, Aming,Cao, Meiping,Feng, Liandong,Dong, Wei
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p. 665 - 667
(2014/01/17)
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- Salen complex of Cu(II) supported on superparamagnetic Fe3O 4@SiO2 nanoparticles: An efficient and recyclable catalyst for synthesis of 1- and 5-substituted 1H-tetrazoles
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An efficient and general method has been developed for synthesis of 1- and 5-substituted 1H-tetrazoles from nitriles and amines using magnetite nanoparticles immobilized Salen Cu(II) as an efficient and recyclable catalyst. The structural and magnetic properties of functionalized magnetic silica are identified by transmission electron microscopy (TEM), scanning electron microscopy (SEM) and vibrating sample magnetometer (VSM) instruments. NMR, FT-IR, elemental analysis and XRD were also used for identification of these structures. Nanocatalyst can be easily recovered by a magnetic field and reused for subsequent reactions for at least 7 times with less deterioration in catalytic activity.
- Dehghani, Farzaneh,Sardarian, Ali Reza,Esmaeilpour, Mohsen
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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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- Synthesis, insecticidal activities, and SAR studies of novel pyridylpyrazole acid derivatives based on amide bridge modification of anthranilic diamide insecticides
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Anthranilic diamides are one of the most important classes of modern agricultural insecticides. To discover new structure-modified compounds with high activity, series of novel carbonyl thioureas, carbonyl ureas, oxadiazoles, carbonyl thiophosphorylureas, oxadiazole-containing amides, and thiazoline-containing amides were designed through the modification of the amide bridge based on the structure of chlorantraniliprole and were synthesized, and bioassays were carried out. The compounds were characterized and confirmed by melting point, IR, 1H NMR, and elemental analyses or HRMS. Preliminary bioassays indicated that some compounds exhibited significant insecticidal activities against oriental armyworm, diamondback moth, beet armyworm, corn borer, and mosquito. Among them, trifluoroethoxyl-containing carbonyl thiourea 20a showed best larvicidal activity against oriental armyworm, with LC50 and LC95 values of 0.1812 and 0.7767 mg/L, respectively. Meanwhile, 20c and 20e showed 86 and 57% death rates against diamondback moth at 0.005 mg/L, and the LC50 values of the two compounds were 0.0017 and 0.0023 mg/L, respectively, which were lower than that of the control chlorantraniliprole. The relationship between structure and insecticidal activity was discussed, and the HF calculation results indicated that the carbonyl thiourea moiety plays an important role in the insecticidal activity. The present work demonstrated that the trifluoroethoxyl-containing carbonyl thioureas can be used as lead compounds for further development of novel insecticides.
- Wang, Bao-Lei,Zhu, Hong-Wei,Ma, Yi,Xiong, Li-Xia,Li, Yong-Qiang,Zhao, Yu,Zhang, Ji-Feng,Chen, You-Wei,Zhou, Sha,Li, Zheng-Ming
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p. 5483 - 5493
(2013/07/27)
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- One-step synthesis of 5-substituted 1 H -Tetrazoles from an aldehyde by reaction with acetohydroxamic acid and sodium azide under Bi(OTf)3 Catalysis
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An efficient one-step method for the synthesis of 5-substituted 1H-tetrazoles from aldehydes by reaction with acetohydroxamic acid and sodium azide using bismuth(III) triflate as the catalyst is described. Georg Thieme Verlag Stuttgart · New York.
- Sridhar, Madabhushi,Mallu, Kishore Kumar Reddy,Jillella, Raveendra,Godala, Kondalreddy,Beeram, Chinaramanaiah,Chinthala, Narsaiah
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p. 507 - 510
(2013/03/28)
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- Zeolite and sulfated zirconia as catalysts for the synthesis of 5-substituted 1H-tetrazoles via [2+3] cycloaddition of nitriles and sodium azide
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The [2+3] cycloaddition between various nitriles and sodium azide proceeds smoothly in the presence of zeolite and sulfated zirconia as effective catalysts, in water and DMF/MeOH, to give the corresponding 5-substituted 1H-tetrazoles in good to high yields. The reaction most probably proceeds through the in situ formation of catalyst azide species, followed by a successive [2+3] cycloaddition with the nitriles. This method has the advantages of high yields, simple methodology and easy work-up. The catalyst can be recovered by simple filtration and reused with good yields.
- Teimouri, Abbas,Najafi Chermahini, Alireza
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experimental part
p. 2606 - 2610
(2011/10/09)
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- Ionic liquid-assisted synthesis of 5-monoand 1,5-disubstituted tetrazoles
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Interaction of aliphatic, aromatic and heteroaromatic nitriles with NaN3 or activated nitriles with organic azides in ionic liquids affords the corresponding 5-mono- and 1,5-disubstituted tetrazoles, ionic liquids functioning both as a reaction medium and as a catalyst.
- Epishina, Margarita A.,Kulikov, Alexander S.,Ignat'Ev, Nikolai V.,Schulte, Michael,Makhova, Nina N.
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experimental part
p. 334 - 336
(2012/01/14)
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- Simple and efficient synthesis of 5-substituted 1-H-tetrazoles using metal-modified clay catalysts
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The synthesis of 5-substituted 1-H-tetrazoles based on reaction of a series of aromatic nitriles with sodium azide was investigated. The reaction was catalyzed by modified montmorillonite K-10 including Cu2+, Fe 3+, Ni2+, and Zn2+ metal ions. The best results obtained by Mont-K10-Cu catalyst. The catalysts were reused several times without loss of their activity. The present procedure offers advantages such as a shorter reaction time, simple workup, recovery, and reusability of the catalyst.
- Chermahini, Alireza Najafi,Teimouri, Abbas,Moaddeli, Ali
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experimental part
p. 168 - 173
(2011/10/08)
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- Tetrazoles: LVI. Synthesis of 5-substituted tetrazoles under microwave activation in the presence of heterogeneous catalyst (Zinc oxide)
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Reactions of aromatic and heteroaromatic nitriles with sodium azide in the presence of zinc oxide under the conditions of microwave activation provide 5-aryl(hetaryl)tetrazoles in high yields. Pleiades Publishing, Ltd., 2011.
- Myznikov,Efimova, Yu. A.,Artamonova,Koldobskii
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experimental part
p. 728 - 730
(2011/08/06)
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- Clay-catalyzed synthesis of 5-substituent 1-H-tetrazoles
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In this study, the possibility of 5-substituted 1-H-tetrazoles synthesis using clays as catalyst was investigated. The reaction of a series of aromatic nitriles with sodium azide was catalyzed by montmorillonite K-10 or kaolin clays in water or DMF as solvent. Conventional heating or ultrasonic irradiation was used to promote reaction. The amount of nitrile to sodium azide mole ratio, amount of catalyst, reaction time, and solvent type were optimized. The versatility of this method was checked by using various nitriles, which showed reasonable yields of tetrazole formation. It was found that using nitriles with electron-with-drawing groups result in both higher yields and lower reaction times. The catalysts could be reused several times without significant loss of their catalytic activity. Compared to conventional heating, ultrasonic irradiation reduced reaction times and increased catalyst activity. The present procedure is green and offers advantages, such as shorter reaction time, simple workup, and recovery and reusability of catalyst.
- Chermahini, Alireza Najafi,Teimouri, Abbas,Momenbeik, Fariborz,Zarei, Amin,Dalirnasab, Zeinab,Ghaedi, Aseyeh,Roosta, Mostafa
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experimental part
p. 913 - 922
(2010/09/03)
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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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- Synthesis of 5-substituted lH-tetrazoles from nitriles and hydrazoic acid by using a safe and scalable high-temperature microreactor approach
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Harnessing hydrazoic acid in a microreactor! Tetrazoles have been synthesized in a very efficient manner by using a high-temperature/high-pressure process intensification regime. Despite the toxic and explosive nature of hydrazoic acid, the synthesis was conducted safely in continuous flow format with residence times as short as 2.5 minutes at 260□°C (see picture).
- Gutmann, Bernhard,Roduit, Jean-Paul,Kappe, C. Oliver,Roberge, Dominique
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supporting information; experimental part
p. 7101 - 7105
(2010/11/05)
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- Synthesis of [5-(1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazol-2-yl]pyridines
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2-, 3-, and 4-[5-(1-Aryl-5-R-1H-1,2,3-triazol-4-yl)-1,3,4-oxadiazol-2-yl] pyridines were synthesized from the corresponding 1-aryl-5-R-1H-1,2,3-triazole- 4-carbonyl chlorides and 2-, 3-, and 4-(1H-tetrazol-5-yl)-pyridines.
- Pokhodylo,Shiika,Matiichuk,Obushak
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scheme or table
p. 417 - 421
(2010/09/20)
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- Novel macrolides and ketolides having antimicrobial activity
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The present invention provides compounds having antimicrobial activity for preventing and treating diseases caused by microbial infections. Thus, the present invention relates to novel semi-synthetic 11,12-γ lactone macrolides and ketolides having antimicrobial activity, processes for making compounds as well as pharmaceutical compositions containing said compounds as active ingredients and methods of treating microbial infections with the compounds.
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Page/Page column 45
(2009/10/06)
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- FeCl3-SiO2 as a reusable heterogeneous catalyst for the synthesis of 5-substituted 1H-tetrazoles via [2+3] cycloaddition of nitriles and sodium azide
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An efficient method for the preparation of 5-substituted 1H-tetrazole derivatives is reported using FeCl3-SiO2 as an effective heterogeneous catalyst. This method has the advantages of high yields, simple methodology, and easy work-up. The catalyst can be recovered by simple filtration and reused delivering good yields.
- Nasrollahzadeh, Mahmoud,Bayat, Yadollah,Habibi, Davood,Moshaee, Saeed
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experimental part
p. 4435 - 4438
(2009/11/30)
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- NOVEL MACROLIDES AND KETOLIDES HAVING ANTIMICROBIAL ACTIVITY
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The present invention provides compounds having antimicrobial activity for preventing and treating diseases caused by microbial infections. Thus, the present invention relates to novel ? semi-synthetic 11,12-γ lactone macrolides and ketolides having antimicrobial activity, processes for making compounds as well as pharmaceutical compositions containing said compounds as active ingredients and methods of treating microbial infections with the compounds.
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Page/Page column 84
(2008/06/13)
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- Amberlite IRA900F as a solid fluoride source for a variety of organic transformations under solvent-free conditions
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We have reported that Amberlite IRA900F (Amb-F) is an efficient metal-free catalyst for the activation of Si-N and Si-O bonds and a mild base in a variety of organic transformations under solvent-free conditions, such as the addition of TMSN3 to (E)-2-aryl-1-cyano-1-nitroethenes, nitriles, α,β-unsaturated acids and their esters, and the addition of dimethylsilyl ketene acetal and ethyl nitroacetate to β-nitrostyrenes. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.
- Fringuelli, Francesco,Lanari, Daniela,Pizzo, Ferdinando,Vaccaro, Luigi
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experimental part
p. 3928 - 3932
(2009/04/08)
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- THE USE OF SELECTIVE P2X7 RECEPTOR ANTAGONISTS
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The present invention relates to the use of selective P2X7 receptor antagonists of formula (I), or a pharmaceutically acceptable salt or prodrug thereof wherein D, R1 and R2 are as defined in claim 1, for the treatment of neuropathic pain, chronic inflammatory pain, inflammation, neurodegeneration and for promoting neuroregeneration.
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Page/Page column 25
(2008/06/13)
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- 5-Substituted, 6-substituted, and unsubstituted 3-heteroaromatic pyridine analogues of nicotine as selective inhibitors of cytochrome P-450 2A6
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A series of 5- and 6-substituted and unsubstituted 3-heteroaromatic analogues of nicotine were synthesized in an effort to delineate the structural requirements for selectively inhibiting human cytochrome P-450 (CYP) 2A6, the major nicotine metabolizing enzyme. Thiophene, substituted thiophene, furan, substituted furan, imidazole, substituted imidazole, pyridine, substituted pyridine, thiazole, and quinoline moieties were used to replace the N-methylpyrrolidine ring of nicotine. Bromo and methyl groups were introduced at the 5-position of the pyridine ring and fluoro, chloro, and methoxy groups were placed at the 6-position of the pyridine ring in order to explore the structure-activity relationship (SAR) of inhibition of CYP2A6. The inhibitory activity of the most potent CYP2A6 inhibitors on the functional activity of human cytochrome P450s 3A4, 2E1, 2B6, 2C9, 2C19, and 2D6 was also examined to determine inhibitor selectivity. We identified 36 compounds that were more potent than nicotine at inhibition of coumarin 7-hydroxylase (CYP2A6) activity. We also found a number of compounds to be highly selective for the inhibition of human CYP2A6 versus the other human CYPs examined.
- Denton, Travis T.,Zhang, Xiaodong,Cashman, John R.
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p. 224 - 239
(2007/10/03)
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- SYNTHETIC COMPOUNDS AND DERIVATIVES AS MODULATORS OF SMOKING OR NICOTINE INGESTION AND LUNG CANCER
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Disclosed are nicotine-related compounds that selectively inhibit cytochrome P-450 2A6 (CYP2A6), selectively inhibit cytochrome P-450 2A13 (CYP2A13), and/or selectively modulate a nicotinic acetylcholine receptor (nAChR). Also disclosed are pharmaceutical compositions comprising a compound of the invention, as well as methods of using the pharmaceutical compositions for treating or preventing a disease or disorder associated with nicotine-ingestion, or a disease or disorder amenable to treatment by selective modulation of nAChRs.
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Page/Page column 113
(2010/02/12)
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- TBAF-Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles under Solventless Conditions
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Tetrabutylammonium fluoride (TBAF) is an efficient catalyst in the [3 + 2] cycloaddition reaction of organic nitriles 1 with trimethylsilyl azide (TMSN3) in solventless conditions. The corresponding 5-substituted 1H-tetrazoles 2 were obtained under mild conditions and in 80-97% yields.
- Amantini, David,Beleggia, Romina,Fringuelli, Francesco,Pizzo, Ferdinando,Vaccaro, Luigi
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p. 2896 - 2898
(2007/10/03)
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- Fast microwave-assisted preparation of aryl and vinyl nitriles and the corresponding tetrazoles from organo-halides
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Aryl and vinyl nitriles have been prepared in very high yields from the corresponding bromides using palladium-catalyzed reactions with microwave irradiation employed as the energy source. Furthermore, flash heating was used successfully for the conversion of these nitriles into aryl and vinyl tetrazoles by cycloaddition reactions. One-pot transformation of aryl halides directly to the aryl tetrazoles could be accomplished both in solution and on solid support. All reactions were completed in minutes rather than in hours or days as previously reported with the standard thermal heating technique. A very potent HIV-1 protease inhibitor (K(i) = 0.56 nM), comprising two tetrazole heterocycles as carboxyl group bioisosteres, was prepared in one pot by microwave-promoted cyanation of a bromo precursor and a subsequent cycloaddition reaction. The temperature-time profiles at 13, 20, and 60 W magnetron input power in DMF are presented.
- Alterman,Hallberg
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p. 7984 - 7989
(2007/10/03)
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- SYNTHESIS OF SOME 5-ARYL(HETARYL)TETRAZOLES BY ULTRASONICATION
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The influence of ultrasound of the 1,3-dipolar cycloaddition of azides to organic nitriles to form of 1H-5-aryl(hetaryl)tetrazoles was studied.It was shown that ultrasound decreases the reaction time, and increases the yield of the desired compounds.
- Pusinov, G. L.,Ishmetova, R. I.,Kitaeva, V. G.,Beresnev, D. G.
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p. 1192 - 1194
(2007/10/03)
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