16289-54-6Relevant articles and documents
The synthesis of 5-substituted 1H-tetrazoles in molten tetrabutylammonium bromide
Xie, Aming,Cao, Meiping,Feng, Liandong,Dong, Wei
, p. 665 - 667 (2013)
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
Safe and efficient tetrazole synthesis in a continuous-flow microreactor
Palde, Prakash B.,Jamison, Timothy F.
, p. 3525 - 3528 (2011)
Safer flow: The synthesis of 5-substituted tetrazoles in flow (see scheme) is safe, efficient, scalable, requires no metal promoter, and uses a near-equimolar amount of NaN3, yet nonetheless displays a broad substrate scope. The hazards associated with HN3 are essentially eliminated, shock-sensitive metal azides such as Zn(N3)2 are avoided, and residual NaN3 is quenched in-line with NaNO 2. Copyright
Why is tetrazole formation by addition of azide to organic nitriles catalyzed by zinc(II) salts?
Himo, Fahmi,Demko, Zachary P.,Noodleman, Louis,Sharpless, K. Barry
, p. 9983 - 9987 (2003)
The mechanism by which zinc(II) catalyzes the union of an azide ion with organic nitriles to form tetrazoles is investigated by means of density functional theory using the hybrid functional B3LYP. The calculations indicate that coordination of the nitril
A new class of iridium(III) complexes based on fluorine substituted 2,3′-bipyridine and pyridyltetrazolate derivatives: Synthesis, crystal structures, photoluminescent and electroluminescent properties
Liu, Denghui,Luo, Kaijun,Ni, Hailiang,Wang, Haifeng,Yang, Bo,Yang, Congling,Yu, Wenhao,Zeng, Longwei,Zhu, Weiguo
, (2020)
The new cyclometalated iridium (III) complexes, (dfpypy)2Ir(BrPyTz) (a), (dfpypy)2Ir(CF3PyTz) (b), (tfpypy)2Ir(CF3PyTz) (c), and (dfpypy)2Ir(PzTz) (d), containing fluorine-substitued 2,3′-bipyridine as the main ligands and pyridyltetrazolate or pyrazinyltetrazolate derivatives as ancillary ligand were synthesized and characterized. The investigation of the crystal structures shows that there are intermolecular interactions in the iridium (III) complexes, including π - π stacking, the weak non - classical C–H?N hydrogen bonds and F … π interactions. Moreover, the UV–vis spectra display concentration-dependent character. As the solution concentration increases, two weak lower-energy absorption bands appear, suggesting there are aggregates between the ground state molecules. All complexes, except d that has emission peak at 467 nm, exhibit the blue photoluminescence (PL) with emission peak at about 440 nm in dichloromethane solution, but the films doped 10 wt % the complexes in polymethyl methacrylate (PMMA) show widened and distinctly tailed PL spectra between 500 and 650 nm, indicating there are the emission originated from aggregates. The organic light-emitting diodes (OLEDs) using a as emitters were fabricated by the vacuum evaporation process. Interestingly, we found that OLEDs doped with 5 wt % a show the voltage-dependent electroluminescent (EL) characteristics. At lower driving voltage EL spectra are basically the same as PL spectra in the solutions, the devices exhibit blue emission with Commission Internationale de L'Eclairage (CIE) coordinates of (0.23,0.32). On the other hand, at higher driving voltage in addition to blue emission from the monomer, there is the broadened red-shifted emission with a peak value of 560 nm originated from the aggregates. The emission from the monomer and the aggregates are well matched to produce white OLEDs with CIE coordinates (0.33,0.39). Furthermore, as the applied voltage is further increased, the blue emission from the monomer is suppressed efficiently and the devices display the yellow emission derived from the aggregates with CIE value of (0.44,0.45).
Synthesis, crystal structure and catalytic property of a new samarium compound derived from 5-(pyrazin-2-yl)tetrazole-2-acetic acid
Zou, Jian-Hua,Chen, Dian-Yu,Yang, Gao-Wen,Li, Qiao-Yun,Yang, Jie,Shen, Lei
, p. 27887 - 27890 (2015)
[Sm(pztza)2(H2O)6]·pztza·3H2O has been prepared by the reaction of SmCl3·6H2O and 5-(pyrazin-2-yl)tetrazole-2-acetic acid (Hpztza) under the presence of potassium hydroxide. The compound has been structurally characterized by elemental analysis, IR, and single-crystal X-ray diffraction. The X-ray analysis demonstrates this complex displays a mononuclear structure. Furthermore, it shows an excellent catalytic property for polymerization of vinyl monomers and the polymerization shows controlled characteristics. It can be isolated from the reaction system and reused at least 10 times.
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
Gajurel, Sushmita,Dam, Binoyargha,Bhushan, Mayank,Singh, L. Robindro,Pal, Amarta Kumar
, (2021/12/09)
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
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
Ashraf, Muhammad Aqeel,Liu, Zhenling,Li, Cheng,Zhang, Dangquan
, (2020/12/23)
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.
5-Aryltetrazoles from Direct C-H Arylation with Aryl Bromides
Zhang, Yuan,Lee, Jack Chang Hung,Reese, Matthew R.,Boscoe, Brian P.,Humphrey, John M.,Helal, Christopher J.
, p. 5718 - 5723 (2020/05/19)
A mild, direct C-H arylation of 1-substituted tetrazoles to 5-aryltetrazoles is developed using a Pd/Cu cocatalytic system with readily available aryl bromides. The methodology avoids late-stage usage of azides and tolerates a wide range of functionalities.
Urea mediated 5-substituted-1H-tetrazole via [3?+?2] cycloaddition of nitriles and sodium azide
Yakambram,Jaya Shree,Srinivasula Reddy,Satyanarayana,Naveen,Bandichhor, Rakeshwar
supporting information, p. 445 - 449 (2018/01/03)
A simple, new and convenient metal free procedure for the synthesis of 5-substituted 1H-tetrazoles using various nitriles and sodium azide in the presence of urea and acetic acid with good to high yields is developed. The reaction plausibly proceeds through in situ formation of urea azide active complex without toxic and/or expensive metal catalysts.
Antibacterial assessment of heteroaryl, Vinyl, Benzyl, and Alkyl tetrazole compounds
Dudley, Joshua,Feinn, Liana,Defrancesco, Heather,Lindsay, Erica,Coca, Adiel,Roberts, Elizabeth Lewis
, p. 550 - 555 (2018/08/17)
Background: In previous reports, the antibacterial properties of certain tetrazole derivatives have been described. We have previously reported the antibacterial properties of aryl 1H-tetrazole compounds. Objective: To study the antibacterial activity of 5-substituted heteroaryl, vinyl, benzyl, and alkyl 1H-tetrazole derivatives. Methods: The antibacterial properties of heteroaryl, vinyl, benzylic, and aliphatic tetrazole derivatives were investigated against Escherichia coli, Staphylococcus aureus, and Pseudomonas aeruginosa. The activity was assessed by determining the minimum inhibitory concentration of these tetrazole derivatives and comparing them to the known antibiotics amoxicillin, trimethoprim and sulfamethoxazole. Results: The tetrazole compounds were prepared utilizing cerium(III) chloride heptahydrate catalysis at 160o C for 1-4 h in a microwave reactor using an aqueous solvent mixture. The most active derivatives exhibited minimum inhibitory concentration values between 125-250 μg/mL against Escherichia coli. More importantly, these compounds were considerably more active when used in combination with trimethoprim and a significant synergistic effect was observed (MIC = 0.98-7.81 μg/mL) against E. coli and S. aureus. Conclusion: The tetrazole derivatives were synthesized in high yield and short reaction times in water. Several of the tetrazole compounds showed a significant synergistic antibacterial effect when used with trimethoprim.
