208264-85-1Relevant articles and documents
Tetrazoles: LVI. Synthesis of 5-substituted tetrazoles under microwave activation in the presence of heterogeneous catalyst (Zinc oxide)
Myznikov,Efimova, Yu. A.,Artamonova,Koldobskii
, p. 728 - 730 (2011)
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.
Application of a functionalized mesoporous silica catalyst to the synthesis of tetrazoles
Najafi Chermahini, Alireza,Khani Omran, Masoud,Dabbagh, Hossein A.,Mohammadnezhad, Gholamhossein,Teimouri, Abbas
, p. 4814 - 4820 (2015)
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.
Construction of six new coordination complexes with 5-(3-pyridyl) tetrazole-2-acetato
Zou, Jian-Hua,Zhu, Da-Liang,Tian, He,Li, Fei Fei,Zhang, Fei Fei,Yang, Gao-Wen,Li, Qiao-Yun,Miao, Yun Xia
, p. 87 - 94 (2014)
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.
Enantiomerism, diastereomerism and thermochromism in two Cu7I4 cluster-based coordination polymers
Liao, Wei-Ming,Li, Xiang-Nan,Zeng, Qi,Zhong, Yuan-Hui,Yin, Ye-Gao,He, Jun
, p. 15136 - 15140 (2019)
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.
Synthesis of 5-Substituted 1 H-Tetrazoles from Nitriles by Continuous Flow: Application to the Synthesis of Valsartan
Carpentier, Florian,Felpin, Fran?ois-Xavier,Zammattio, Fran?oise,Le Grognec, Erwan
, p. 752 - 761 (2020/03/13)
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.
Synthesis and Photochemical Properties of Manganese(I) Tricarbonyl Diimine Complexes Bound to Tetrazolato Ligands
Stout, Matthew J.,Stefan, Alessandra,Skelton, Brian W.,Sobolev, Alexandre N.,Massi, Massimiliano,Hochkoeppler, Alejandro,Stagni, Stefano,Simpson, Peter V.
supporting information, p. 292 - 298 (2020/01/25)
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.
Iron (III)-porphyrin Complex FeTSPP as an efficient catalyst for synthesis of tetrazole derivatives via [2?+?3]cycloaddition reaction in aqueous medium
El-Remaily, Mahmoud Abd El Aleem Ali Ali,Elhady
, (2019/06/08)
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.
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
Nasrollahzadeh, Mahmoud,Ghorbannezhad, Fatemeh,Sajadi, S. Mohammad
, (2018/12/14)
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.
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
Sharma, Swagat,Kozek, Krystian A.,Abney, Kristopher K.,Kumar, Sushil,Gautam, Nagsen,Alnouti, Yazen,David Weaver,Hopkins, Corey R.
, p. 791 - 796 (2019/02/06)
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.
Syntheses and characterization of dinuclear and tetranuclear AgI supramolecular complexes generated from symmetric and asymmetric molecular clips containing oxadiazole rings
Jin, Guoxia,Ji, Yuqi,Wang, Teng,Sun, Yanyan,Li, Yulong,Zhu, Guiying,Ma, Jianping
, p. 1327 - 1335 (2019/10/19)
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.
