3250-74-6

Usage

Uses

Used in Pharmaceutical Industry:
3-(2H-TETRAZOL-5-YL)-PYRIDINE is used as a pharmaceutical intermediate for the synthesis of various drugs. Its unique structure allows it to participate in a range of chemical reactions, making it a versatile building block in the development of new medications.
Used in Synthesis of 1-(4-bromo-phenyl)-3-(5-pyridin-3-yl-tetrazol-2-yl)-propan-1-one:
3-(2H-TETRAZOL-5-YL)-PYRIDINE is used as a reactant in the synthesis of 1-(4-bromo-phenyl)-3-(5-pyridin-3-yl-tetrazol-2-yl)-propan-1-one, a compound with potential pharmaceutical applications. The reaction involves the use of 1-(4-bromo-phenyl)-3-piperidino-propan-1-one, hydrochloride, and dimethylformamide as a solvent. The process requires a reaction time of 8 hours at a temperature of 150°C, yielding a product with a 31% yield.

InChI:InChI=1/C6H4N5/c1-2-5(4-7-3-1)6-8-10-11-9-6/h1-4H/q-1

Upstream product

• 1120-90-7 3-iodopyridine 
• 1193-92-6 3-pyridinealdoxime 
• 500-22-1 3-pyridinecarboxaldehyde 
• 626-55-1 3-Bromopyridine 
• 100-54-9 pyridine-3-carbonitrile 
• 4648-54-8 trimethylsilylazide 

Downstream Products

• 1352548-02-7 C₁₄H₁₁ClN₄O 
• 1438853-59-8 C₂₄H₁₅BrCl₂N₈O₃ 
• 1352547-98-8 C₂₄H₁₅Cl₃N₈O₂S 
• 21398-08-3 3-(5-phenyl-1,3,4-oxadiazol-2-yl)pyridine 
• 89546-87-2 2-methyl-5-(pyridin-3-yl)-1,3,4-oxadiazole 
• 104186-22-3 2,6-Dimethyl-4-(5-pyridin-3-yl-tetrazol-2-ylmethyl)-phenol 

Relevant academic research and scientific papers

Synthesis of 5-Substituted 1 H-Tetrazoles from Nitriles by Continuous Flow: Application to the Synthesis of Valsartan

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

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

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.

Enantiomerism, diastereomerism and thermochromism in two Cu7I4 cluster-based coordination polymers

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.

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

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

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

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.

Synthesis, molecular docking and xanthine oxidase inhibitory activity of 5-aryl-1H-tetrazoles

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

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

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.

Piperazinium dihydrogen sulfate: An acidic ionic liquid for the [3+2] cycloaddition reaction of sodium azide with organic nitriles

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.