cas 14389-12-9, 5-(4-PYRIDYL)-1H-TETRAZOLE

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1-Disulfo-[2,2-bipyridine]-1,1-diium chloride ionic liquid as an efficient catalyst for the green synthesis of 5-substituted 1H-tetrazoles
A simple, green and efficient method has been developed for the synthesis of 5-substituted 1H-tetrazole derivatives through [2+3] cycloaddition reaction in good to excellent yields between various benzonitriles and sodium azide. For this purpose, 1-disulfo-[2,2-bipyridine]-1,1-diium chloride ([BiPy](HSO3)2Cl2) system as an ionic liquid catalyst have been extended for the construction of these valuable products. This procedure has significant advantages, including using ethylene glycol as a green solvent. The other advantages of this method are inexpensive and ease the preparation of the catalyst, mild reaction conditions, green reaction medium, easy workup, short reaction time, and simple experimental process.
Aali, Elaheh,Gholizadeh, Mostafa,Noroozi-Shad, Nazanin
(2021/08/30)

PROCESS FOR PREPARING 5-SUBSTITUTED-1H-TETRAZOLES IN AQUEOUS BETAINE SOLUTION
The present invention relates to a method for manufacturing 5-substituted-1H-tetrazole in an aqueous betaine solution. More specifically, the present invention relates to a method for manufacturing 5-substituted-1H-tetrazole which comprises: a step of con
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Paragraph 0091-0096

(2020/06/13)

Novel Hybrid Thioamide Ligand Supported Copper Nanoparticles on SBA-15: A Copper Rich Robust Nanoreactor for Green Synthesis of Triazoles and Tetrazoles in Water Medium
Abstract: In this work, a new thioamide based ligand with reductive nature was designed for modification of mesoporous SBA-15. For this purpose, the channels of SBA-15 were modified with Tris(2-aminoethyl)amine (TAEA) groups and then reacted with S8 and phenyl acetylene to form thioamide groups via Willgerodt-Kindler reaction. This porous material proved to be an effective host for the immobilization of inexpensive Cu(II) ions. The catalytically active Cu(I) species were generated automatically due to the reductive nature of thioamide modified surface of catalyst without use of any toxic reducing agents. The well stabilized Cu(I) species into the nano-channels of SBA-15 were used for synthesis of various triazoles from sodium azide, phenyl acetylene and alkyl/benzyl halides or alkyl epoxides and various tetrazoles from sodium azide and aryl/alkyl nitriles under green mild aqueous reaction conditions. This catalytic system was used for 9 and 11 consecutive runs for synthesis of triazoles and tetrazoles, respectively. Graphic Abstract: [Figure not available: see fulltext.]
Pourhassan, Fatemeh,Eshghi, Hossein
p. 1287 - 1300
(2019/11/21)

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.
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)

Bivalent zinc ion metal organic complex as well as preparation method and application thereof (by machine translation)
The invention relates to a divalent zinc ion metal organic complex and a preparation method and application, and firstly, an organic ligand L, and a structural formula thereof are prepared firstly: The solution of the organic ligand L and the zinc salt solution react at room temperature to obtain the metal organic complex, and the metal organic complex serves as a catalyst to catalyze the synthesis of diisopropyl - D D-mannitol to have a good catalytic effect. (by machine translation)
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Paragraph 0014; 0060-0062; 0065-0067; 0069-0071

(2019/09/17)

Syntheses, structures and catalytic mechanisms of three new MOFs for aqueous Cr(VI) reduction and dye degradation under UV light
Three novel metal–organic frameworks (MOFs) photocatalysts with different structures [Cd(4-Hptz)2(H2O)2Cl2](4-Hptz = 4-(1H-tetrazol-5-yl)-pyridine) (1), [Cu(btx)2(ClO4)2]n/
Wang, Liwen,Zeng, Tianyu,Liao, Guiying,Cheng, Qingrong,Pan, Zhiquan
supporting information
p. 152 - 162
(2018/10/24)

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.
Nasrollahzadeh, Mahmoud,Ghorbannezhad, Fatemeh,Sajadi, S. Mohammad
(2018/12/14)

Synthesis of α-Aminonitriles and 5-Substituted 1H-Tetrazoles Using an Efficient Nanocatalyst of Fe3O4@SiO2–APTES-supported Trifluoroacetic Acid
Fe3O4@SiO2–APTES-supported trifluoroacetic acid nanocatalyst was used for the one-pot synthesis of α-aminonitriles via a three-component reaction of aldehydes (or ketones), amines, and sodium cyanide. This method produced a high yield of 75–96% using only a small amount of the catalyst (0.05?g) in EtOH at room temperature. The catalyst was also employed for the synthesis of 5-substituted 1H-tetrazoles from nitriles and sodium azide in EtOH at 80°C. The tetrazoles were produced with good-to-excellent yields in a short reaction time of 4?h. Both synthetic methods were carried out in the absence of an organic volatile solvent. Because the supported trifluoroacetic acid generated a solid acid on the surface, thus the acid corrosiveness was not a serious challenge. This heterogeneous nanocatalyst was magnetically recovered and reused several times without significant loss of catalytic activity.
Fatahi, Hosna,Jafarzadeh, Mohammad,Pourmanouchehri, Zahra
p. 2090 - 2098
(2019/07/05)

Enhanced Thermocatalytic Activity of Porous Yellow ZnO Nanoflakes: Defect- and Morphology-Induced Perspectives
Herein, we report a simple and effective strategy for the synthesis of yellow ZnO (Y-ZnO) nanostructures with abundant oxygen vacancies on a large scale, through the sulfidation of ZnO followed by calcination. The developed strategy allows retention of the overall morphology of Y-ZnO compared with pristine ZnO and the extent of oxygen vacancies can be tuned. The influence of oxygen deficiencies, the extent of defect sites, and the morphology of ZnO on its solution-phase thermocatalytic activity has been evaluated in the synthesis of 5-substituted-1H-tetrazoles with different nitriles and sodium azide. A reasonable enhancement in the reaction rate was achieved by using Y-ZnO nanoflakes (Y-ZnO NFs) as a catalyst in place of pristine ZnO NFs. The reaction was complete within 6 h at 110 °C with Y-ZnO NFs, whereas it took 14 h at 120 °C with pristine ZnO NFs. The catalyst is easy to recycle without a significant loss in catalytic activity.
Galani, Sunil M.,Panda, Asit Baran
p. 612 - 620
(2019/02/14)

Synthesis, crystal structure and investigation of the catalytic and spectroscopic properties of a Zn(II) complex with coumarin-hydrazone ligand
A Zn(II) complex with coumarin-hydrazone ligand, [ZnCl(HL)(CH3OH)0.76(H2O)0.24]·0.24(CH3OH) (1), was synthesized from the reaction of equimolar amount of ZnCl2·4H2O and (E)-2-hyd
Aslkhademi, Sanam,Noshiranzadeh, Nader,Sadjadi, Mirabdullah Seyed,Mehrani, Kheirollah,Farhadyar, Nazanin
p. 115 - 122
(2019/01/08)

Three AgI, CuI and CdII coordination polymers based on the new asymmetrical ligand 2-{4-[(1H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole: syntheses, characterization and emission properties
The new asymmetrical organic ligand 2-{4-[(1H-imidazol-1-yl)methyl]phenyl}-5-(pyridin-4-yl)-1,3,4-oxadiazole (L, C17H13N5O), containing pyridine and imidazole terminal groups, as well as potential oxdiazole coordination si
Jin, Guo-Xia,You, Tian-Chao,Ma, Jian-Ping
p. 1690 - 1697
(2019/12/23)

[3 + 2] Cycloaddition promoted by zinc oxide nanoparticles anchored on reduced graphene oxide using green solvent
ZnO anchored on RGO-catalyzed [3 + 2] cycloaddition of nitriles and sodium azide in the synthesis of 5-substituted 1H-tetrazoles in water is an efficient and simple protocol with low catalyst loading under reflux condition. It is applied to a wide range of substrates with an excellent yield, simple workup procedure, recovery, and reusability of catalyst with consistent activity and high turnover number. It is proposed that the functional groups present in RGO surface are effective for preventing the aggregation of catalytically active ZnO species during the reaction. Moreover, the excellent performance of ZnO–RGO nanocomposite is ascribed to the excellent dispersity of catalyst in water, hydrophilic nature of the RGO for the accumulation of organic substrates in water, and the “Breslow effect.”.
Clarina, Thanaraj,Rama, Velladurai
supporting information
p. 175 - 187
(2018/01/01)

L -Proline: An Efficient Organocatalyst for the Synthesis of 5-Substituted 1 H -Tetrazoles via [3+2] Cycloaddition of Nitriles and Sodium Azide
A simple and efficient route for the synthesis of a series of 5-substituted 1 H -tetrazoles using l -proline as a catalyst from structurally diverse organic nitriles and sodium azide is reported. The prominent features of this environmentally benign, cost effective, and high-yielding l -proline-catalyzed protocol includes simple experimental procedure, short reaction time, simple workup, and excellent yields making it a safer and economical alternative to hazardous Lewis acid catalyzed methods. The protocol was successfully applied to a broad range of substrates, including aliphatic and aryl nitriles, organic thiocyanates, and cyanamides.
Bhagat, Saket B.,Telvekar, Vikas N.
supporting information
p. 874 - 879
(2018/02/16)

Preparation of Ag-doped g-C3N4 Nano Sheet Decorated Magnetic γ-Fe2O3@SiO2 Core–Shell Hollow Spheres through a Novel Hydrothermal Procedure: Investigation of the Catalytic activity for A3, KA2 Coupling Reactions and [3?+?2] Cycloaddition
Taking advantageous of both g-C3N4 and magnetic core-shell hollow spheres, for the first time a heterogeneous and magnetically separable hybrid system was prepared through a novel and simple hydrothermal procedure and used for immobilization of bio-synthesized Ag(0) nanoparticles. The hybrid system was fully characterized by using SEM/EDS, FTIR, VSM, TEM, XRD, TGA, DTGA, ICP-AES, BET and elemental mapping analysis. The catalytic utility of the obtained system, h-Fe2O3@SiO2/g-C3N4/Ag, for promoting ultrasonic-assisted A3, KA2 coupling reactions and [3?+?2] cycloaddition has been confirmed. The results established that the catalyst could efficiently catalyze the reaction to afford the corresponding products in high yields in short reaction times. The reusability study confirmed that the catalyst could be recovered and reused for at least five reaction runs with only slight loss of the catalytic activity. The hot filtration test also proved low silver leaching, indicating the heterogeneous nature of the catalysis.
Sadjadi, Samahe,Malmir, Masoumeh,Heravi, Majid M.
(2018/07/31)

Antibacterial assessment of heteroaryl, Vinyl, Benzyl, and Alkyl tetrazole compounds
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.
Dudley, Joshua,Feinn, Liana,Defrancesco, Heather,Lindsay, Erica,Coca, Adiel,Roberts, Elizabeth Lewis
p. 550 - 555
(2018/08/17)

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
Fatima, Itrat,Zafar, Humaira,Khan, Khalid Mohammed,Saad, Syed Muhammad,Javaid, Sumaira,Perveen, Shahnaz,Choudhary, M. Iqbal
p. 201 - 211
(2018/05/24)

KIT-6-anchored sulfonic acid groups as a heterogeneous solid acid catalyst for the synthesis of aryl tetrazoles
In the current study, a simple, environmentally benign and cost-effective method is presented for the preparation of 5-substituted-1H-aryltetrazoles. To this goal, mesoporous KIT-6 silica anchored with sulfonic acid (–SO3H) groups via post-grafting modification was synthesized using the sol–gel method and characterized by XRD, TGA, FTIR, BET, TEM and SEM techniques. For the preparation of tetrazole derivatives, the effect of various parameters such as catalyst amount, aryl nitrile:azide ratio, temperature and reaction time was tested. The hybrid organic/inorganic catalyst could be recovered easily through a simple filtration and reused multiple times without significant loss in activity.
Najafi Chermahini, Alireza,Andisheh, Nikzad,Teimouri, Abbas
p. 831 - 838
(2018/03/01)

Synthesis, Structure, and Anti-influenza Activity of 2-(Adamantan-1-yl)-5-aryl-1,3,4-oxadiazoles and 2-(Adamantan-1-yl)-5-aryltetrazoles
Two series of new adamantyl derivatives of polynitrogen heterocycles, 2-(adamantan-1-yl)-5-aryl- 1,3,4-oxadiazoles and 2-(adamantan-1-yl)-5-aryl-2H-tetrazoles, have been synthesized, and their structure has been determined by NMR spectroscopy, mass spectr
Seliverstova,Suslonov,Zarubaev,Trifonov
p. 633 - 638
(2018/06/12)

A Magnetically Recoverable and Reusable Catalyst for Synthesis of 5-Substituted 1H-Tetrazoles
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Elhampour, Ali,Nemati, Firouzeh
p. 493 - 501
(2019/01/09)

Design, Synthesis, and Evaluation of the Highly Selective and Potent G-Protein-Coupled Receptor Kinase 2 (GRK2) Inhibitor for the Potential Treatment of Heart Failure
A novel class of therapeutic drug candidates for heart failure, highly potent and selective GRK2 inhibitors, exhibit potentiation of β-adrenergic signaling in vitro studies. Hydrazone derivative 5 and 1,2,4-triazole derivative 24a were identified as hit compounds by HTS. New scaffold generation and SAR studies of all parts resulted in a 4-methyl-1,2,4-triazole derivative with an N-benzylcarboxamide moiety with highly potent activity toward GRK2 and selectivity over other kinases. In terms of subtype selectivity, these compounds showed enough selectivity against GRK1, 5, 6, and 7 with almost equipotent inhibition to GRK3. Our medicinal chemistry efforts led to the discovery of 115h (GRK2 IC50 = 18 nM), which was obtained the cocrystal structure with human GRK2 and an inhibitor of GRK2 that potentiates β-adrenergic receptor (βAR)-mediated cAMP accumulation and prevents internalization of βARs in β2AR-expressing HEK293 cells treated with isoproterenol. Therefore, 115h appears to be a novel class of therapeutic for heart failure treatment.
Okawa, Tomohiro,Aramaki, Yoshio,Yamamoto, Mitsuo,Kobayashi, Toshitake,Fukumoto, Shoji,Toyoda, Yukio,Henta, Tsutomu,Hata, Akito,Ikeda, Shota,Kaneko, Manami,Hoffman, Isaac D.,Sang, Bi-Ching,Zou, Hua,Kawamoto, Tetsuji
p. 6942 - 6990
(2017/09/07)

Development and Demonstration of a Safer Protocol for the Synthesis of 5-Aryltetrazoles from Aryl Nitriles
The search for a faster, safer protocol for the direct synthesis of 5-aryltetrazoles from aryl nitriles in the presence of sodium azide and an amine hydrochloride salt led to the discovery of a buffered system comprised of BnNH2, BnNH2·HCl, and NaN3. After optimization of reaction conditions and a thorough investigation of reaction safety, the procedure was demonstrated for the synthesis of several hundred grams of 4-chloro-2-(2H-tetrazol-5-yl)phenol. The generality of the developed reaction conditions was established by a small-scale reactivity screen using 16 additional aryl and heteroaryl nitrile substrates.
Treitler, Daniel S.,Leung, Simon,Lindrud, Mark
p. 460 - 467
(2017/03/24)

A new class of potential antidiabetic acetohydrazides: Synthesis, in vivo antidiabetic activity and molecular docking studies
Two new pharmacologically active series of tetrazolopyridine-acetohydrazide conjugates [9 (a-n), 10 (a-n)] were synthesized by reacting a variety of suitably substituted benzaldehydes and isomeric 2-(5-(pyridin-3/4-yl)-2H-tetrazol-2- yl)acetohydrazides (7, 8). The synthesized compounds were analyzed through FTIR, 1H NMR, 13C NMR and elemental techniques. These acetohydrazides were screened for their in vivo antidiabetic activity and molecular docking studies. An excellent agreement was obtained as the best docked poses showed important binding features mostly based on interactions due to an oxygen atom and aromatic moieties of the series. The compounds 9a, 9c and 10l were found to be the most active in lowering blood glucose, having the potential of being good antidiabetic agents.
Arif, Mubeen,Jabeen, Furukh,Saeed, Aamer,Qureshi, Irfan Zia,Mushtaq, Nadia
p. 319 - 332
(2017/09/13)

Syntheses of 5-substituted 1H-tetrazoles catalyzed by reusable Cu(II)-NaY zeolite from nitriles
Cu(II)-NaY heterogeneous catalyst is used for the synthesis of 5-substituted 1H-tetrazoles by [2+3]-cycloaddition of sodium azide and nitriles. The salient features of this process are low reaction times, mild reaction conditions and high yields. The catalyst is recovered and reused for several cycles with consistent activity.
Sudhakar,Purna Chandra Rao,Prem Kumar,Suresh,Ravi
p. 864 - 866
(2017/02/10)

Synthesis of 5-substituted-1H-tetrazole derivatives using monodisperse carbon black decorated Pt nanoparticles as heterogeneous nanocatalysts
A facile and highly efficient protocol for synthesis of new 5-substituted 1H-tetrazoles derivatives has been developed by the assistance of vulcan carbon decorated based on monodisperse platinum nanoparticles (Pt NPs@VC) as superior and recyclable heterog
Baskaya, Gaye,Esirden, Ibrahim,Erken, Esma,Sen, Fatih,Kaya, Muharrem
p. 1992 - 1999
(2017/01/28)

Cu(II) immobilized on Fe3O4@APTMS-DFX nanoparticles: An efficient catalyst for the synthesis of 5-substituted 1: H -tetrazoles with cytotoxic activity
Cu(ii) immobilized on deferasirox loaded amine functionalized magnetic nanoparticles (Cu(ii)/Fe3O4@APTMS-DFX) as a novel magnetically recyclable heterogeneous catalyst is able to catalyze the [3 + 2] cycloaddition reactions of various organic nitriles with sodium azide. Using this method, a series of 5-substituted-1H-tetrazoles under mild conditions in DMSO were prepared. The reaction involves mild reaction conditions with efficient transformation capability. The developed catalyst could be easily separated by applying an external magnetic field. Furthermore, it could be recycled for 5 runs with negligible leaching of copper from the surface of the catalyst. The catalyst was characterized by various techniques such as FT-IR, TGA, VSM, SEM-EDX, and ICP-OES. Several derivatives of 1H-tetrazoles were prepared using this catalyst, and their structures were confirmed using different techniques. Then, the synthesized anthraquinones were evaluated for their cytotoxicity against several cell lines including MCF-7, MAD-MD-231, HT-29, HeLa, neuro-2a and L-929. The results obtained from the MTT assay revealed that the 6 derivatives exhibited a high level of cytotoxicity. In order to determine the cytotoxicity mechanism, 2 derivatives with the highest cytotoxic activity were selected, and an apoptosis assay was carried out by flow cytometry, which supported that apoptosis is the major mechanism.
Taghavi, Faezeh,Gholizadeh, Mostafa,Saljooghi, Amir Sh.,Ramezani, Mohammad
p. 1953 - 1964
(2017/10/27)

Conversion of Arylboronic Acids to Tetrazoles Catalyzed by ONO Pincer-Type Palladium Complex
A convenient synthesis of a library of tetrazoles through a novel and operationally simple protocol effecting the direct conversion of arylboronic acids catalyzed by a new ONO pincer-type Pd(II) complex under mild reaction conditions using the readily available reagents is reported. The palladium complex was reused up to four cycles in an open-flask condition.
Vignesh, Arumugam,Bhuvanesh, Nattamai S. P.,Dharmaraj, Nallasamy
p. 887 - 892
(2018/06/15)

Regioselective and stereoselective route to N2-β-tetrazolyl unnatural nucleosides via SN2 reaction at the anomeric center of Hoffer's chlorosugar
We are reporting a regioselective and stereoselective route to N2-β-tetrazolyl aromatic donor/acceptor unnatural nucleosides as new class of possible DNA base analogs. The SN2 substitution reaction at the anomeric center of Hoffer's chlorosugar with various 5-substituted aromatic tetrazoles in THF in presence of K2CO3 proceeds with regioselectivity at N2-tetrazoles and stereoselectivity at α-chlorosugar with very good yield. The stereoelectronic and steric effects play a crucial role for the observed outcome which is also supported from a theoretical (DFT) study. The methodology is simple, eco-compatible and the tetrazolyl unnatural nucleosides might find applications in decorating DNA for various biotechnological and DNA based material science applications.
Bag, Subhendu Sekhar,Talukdar, Sangita,Anjali
supporting information
p. 2044 - 2050
(2016/04/05)

Nitrogen-rich 5-(4-pyridyl)tetrazole-2-acetic acid and its alkaline earth metal coordination polymers for potential energetic materials
Tetrazole and its derivatives with rich nitrogen atoms may be potential candidates for energetic materials. Alkaline earth metal coordination compounds based on such ligands are relatively less investigated. Hpytza was prepared from 4-cyanopyridine and sodium azide, ethyl bromoacetate, where Hpytza = 5-(4-pyridyl)tetrazole-2-acetic acid. Hpytza and four alkaline earth metal coordination polymers [Mg(pytza)2]n (1), [Ca(pytza)2(H2O)2]n·3nH2O (2), [Sr(pytza)2(H2O)2]n (3) and [Ba(pytza)2(H2O)2]n·nH2O (4) were prepared under solvothermal conditions. The thermal behavior of these compounds were characterized by the differential scanning calorimetry (DSC) and thermogravimetric-differential thermogravimetric (TG-DTG) analyses. Furthermore, the critical temperature of thermal explosion and relevant thermal parameters ΔS, ΔH, ΔG of Hpytza and polymers 1-4 were calculated, as well, indicating that these compounds are potential energetic materials.
Yang, Gao Wen,Zhang, Yuan Ting,Wu, Qi,Cao, Meng Jie,Wu, Jiao,Yue, Qiu Yan,Li, Qiao Yun
p. 364 - 371
(2016/07/06)

Synthesis of 5-substituted 1H-tetrazoles from aryl halides using nanopolymer-anchored palladium(II) complex as a new heterogeneous and reusable catalyst
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.
p. 2135 - 2142
(2016/11/17)

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.
Kumar, Arvind,Kumar, Satyanand,Khajuria, Yugal,Awasthi, Satish Kumar
p. 75227 - 75233
(2016/08/24)

Magnetically separable Fe3O4@chitin as an eco-friendly nanocatalyst with high efficiency for green synthesis of 5-substituted-1H-tetrazoles under solvent-free conditions
The present study describes an efficient, eco-friendly and simple method for the synthesis of 5-substituted-1H-tetrazoles catalyzed by magnetite-chitin (Fe3O4@chitin) as a green and recyclable catalyst. Fe3O4@chitin was initially prepared using hydrothermal synthesis. Subsequently, the structure, morphology, and magnetic properties of the prepared nanocatalyst were studied with some different spectroscopic, microscopic and thermogravimetric techniques such as FT-IR, XRD, SEM, TEM, VSM and TGA. Obtained results showed that Fe3O4@chitin nanoparticles exhibited uniform cubic shape and were well monodispersed. Also, magnetic measurement revealed that the synthesized nanocatalyst had superparamagnetic features. The application of this new nanocatalyst allows the synthesis of a variety of tetrazoles through the reaction of nitriles with 1-butyl-3-methylimidazolium azide ([bmim][N3]) under solvent-free conditions. This synthetic pathway is a green protocol offering significant advantages, such as excellent yield of products in short reaction times, mild reaction conditions, minimization of chemical waste, easy preparation of the catalyst and its recyclability up to six cycles without any considerable loss of efficiency.
Zarghani, Monireh,Akhlaghinia, Batool
p. 31850 - 31860
(2016/04/26)

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.
Nowrouzi, Najmeh,Farahi, Soghra,Irajzadeh, Maryam
p. 113 - 119
(2016/02/27)

Ag-doped nano magnetic γ-Fe2O3@DA core-shell hollow spheres: An efficient and recoverable heterogeneous catalyst for A3 and KA2 coupling reactions and [3 + 2] cycloaddition
An effective protocol for the fabrication of Ag-doped nano magnetic γ-Fe2O3@DA core-shell hollow spheres (h-Fe2O3@DA/Ag) by a simple hydrothermal method is demonstrated without any templates in the reaction system. The synthesized core-shell structure was successfully characterized in terms of the chemical composition, surface morphology, and magnetic properties using FT-IR, VSM, TGA, TEM, FE-SEM, EDS, and XRD patterns. The possible formation mechanism of this magnetic γ-Fe2O3@DA/Ag hollow sphere structure is described based on the experimental results. In addition, as a physical property, the apparent shell density was determined using the specific surface area (BET) and shell thickness (BJH). The important, novel and unique catalyst with a hollow structural character and strong magnetic behavior exhibited a high catalytic activity in the A3 and KA2 coupling reactions and [3 + 2] cycloaddition for the synthesis of 1H-tetrazoles. Furthermore, the recovered catalyst of the reaction mixture was facilitated by a magnetic field and multiple recycling was carried out without any significant loss in the catalytic activity.
Elhampour,Malmir,Kowsari,Boorboor Ajdari,Nemati
p. 96623 - 96634
(2016/10/25)

Activated Fuller's earth as an inexpensive, eco-friendly, efficient catalyst for the synthesis of 5-aryl 1-H-tetrazole via [3+2] cycloaddition of nitriles and sodium azide
A simple and efficient method for the preparation of 5-aryl 1-H-tetrazoles was developed from various aryl nitriles and sodium azide (NaN3) via [3+2] cycloaddition reaction using activated Fuller's earth as an efficient heterogeneous catalyst.
Rekunge, Deelip S.,Indalkar, Krishna S.,Chaturbhuj, Ganesh U.
supporting information
p. 5815 - 5819
(2016/12/06)

RETRACTED ARTICLE: A rapid and novel method for the synthesis of 5-substituted 1H-tetrazole catalyzed by exceptional reusable monodisperse Pt NPs@AC under the microwave irradiation
A series of 5-substituted 1H-tetrazoles were synthesized in DMF by the [3 + 2] cycloaddition reaction under the effect of microwave irradiation (10-30 min, fixed mode, 90 °C, 140 W) in the presence of highly efficient superior catalyst. For this reaction,
Erken, Esma,Esirden, Ibrahim,Kaya, Muharrem,Sen, Fatih
p. 68558 - 68564
(2015/09/01)

RETRACTED ARTICLE: Monodisperse Pt NPs@rGO as highly efficient and reusable heterogeneous catalysts for the synthesis of 5-substituted 1H-tetrazole derivatives
Monodisperse platinum nanoparticles supported on reduced graphene oxide (Pt NPs@rGO) are stable, isolable, bottleable, long-lived, highly efficient and exceptionally reusable heterogeneous catalysts for the synthesis of 5-substituted 1H-tetrazoles from so
Esirden, Ibrahim,Erken, Esma,Kaya, Muharrem,Sen, Fatih
p. 4452 - 4457
(2015/09/01)

A rapid metal free synthesis of 5-substituted-1H-tetrazoles using cuttlebone as a natural high effective and low cost heterogeneous catalyst
A convenient, rapid and metal free synthesis of 5-substituted-1H-tetrazoles is described by [3 + 2] cycloaddition reaction of nitriles with sodium azide. The reaction was catalyzed by cuttlebone in DMSO at 110°C. Cycloaddition reaction of nitriles with sodium azide happened in the presence of mesoporous cuttlebone by "electrophilic activation" of nitriles through hydrogen bond formation between the cuttlebone and nitrile. Cuttlebone as a natural low cost heterogeneous catalyst with high porosity, high flexural stiffness, high compressive strength and high thermal stability affords 5-substituted-1H-tetrazoles rapidly with high efficiency.
Ghodsinia, Sara S. E.,Akhlaghinia, Batool
p. 49849 - 49860
(2015/06/25)

4-(N,N-Dimethylamino)pyridinium acetate as a recyclable catalyst for the synthesis of 5-substituted-1H-tetrazoles
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
p. 739 - 742
(2015/01/30)

Synthesis of 5-substituted 1H-tetrazoles using a recyclable heterogeneous nanonickel ferrite catalyst
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
p. 730 - 735
(2015/11/09)

Cu(ii) immobilized on aminated epichlorohydrin activated silica (CAES): As a new, green and efficient nanocatalyst for preparation of 5-substituted-1H-tetrazoles
Cu(ii) immobilized on aminated epichlorohydrin activated silica (CAES) is a novel and efficient heterogeneous nanocatalyst in the [3 + 2] cycloaddition reactions of various organic nitriles with sodium azide. The protocol can provide a series of 5-substituted-1H-tetrazoles under mild conditions in DMSO. Efficient transformation, mild reaction conditions, easy product isolation and the potential reusability of the catalyst are attractive features. The catalyst (CAES) was characterized by FT-IR, TGA, TEM, BET, SEM-EDS, CHN and ICP techniques.
Razavi, Nasrin,Akhlaghinia, Batool
p. 12372 - 12381
(2015/02/19)

Expanded perlite: An inexpensive natural efficient heterogeneous catalyst for the green and highly accelerated solvent-free synthesis of 5-substituted-1H-tetrazoles using [bmim]N3 and nitriles
A versatile, green and highly accelerated protocol for preparing 5-substituted-1H-tetrazoles is reported. In this method, 5-substituted-1H-tetrazoles are synthesized from nitriles and [bmim]N3, in the presence of the expanded perlite as an inexpensive natural efficient heterogeneous catalyst, under solvent-free condition. A wide variety of aryl nitriles underwent [3 + 2] cycloaddition to afford the desired tetrazoles in good to excellent yields, rapidly. This method has the advantages of high yields, short reaction times, simple methodology, and easy work-up. The catalyst can be recovered by simple filtration and reused delivering good yields.
Jahanshahi, Roya,Akhlaghinia, Batool
p. 104087 - 104094
(2015/12/24)

Facile, highly efficient and novel method for synthesis of 5-substituted 1H-tetrazoles catalysed by copper(I) chloride
The present study on tetrazole compounds, which have a wide area of application, proposes a new, simple and highly effective method. A series of 5-substituted 1H-tetrazoles were synthesised in DMF via the [3 + 2] cycloaddition reaction, in which different
Esirden, Ibrahim,Ba?ar, Erhan,Kaya, Muharrem
p. 1231 - 1236
(2015/06/23)

Rectangular ZnO porous nano-plate assembly with excellent acetone sensing performance and catalytic activity
The controlled synthesis of a hierarchically assembled porous rectangular ZnO plate (2.5-3.5 μm length, 1.5-2.5 μm width and 100-150 nm thickness) from bulk ZnO without using any organic substrates, such as solvents/surfactants/structure-directing agents, is presented. The synthesized ZnO plates are single crystalline with exposed (1010) facets on the flat surface, porous and formed through the calcination of a hydrozincite [Zn5(CO3)2(OH)6] intermediate. A gas sensor based on the synthesized porous ZnO architecture exhibited high sensitivity towards acetone even in low concentration (S = 3.4 in 1 ppm acetone) with good selectivity. The ZnO nanostructured material as a heterogeneous catalyst also showed excellent catalytic activity for the synthesis of 5-substituted-1H-tetrazoles (yield = 94%). Both the activities are superior than those of other reported ZnO based acetone sensors and heterogeneous catalysts. We believe that the improved properties of the synthesized ZnO nanostructure is due to the exposed (1010) facets, and its porous and assembled structure, which provides a reasonably large accessible surface area, and facilitates diffusion and mass transport of gas or substrate molecules.
Giri, Arnab Kanti,Saha, Arka,Mondal, Aniruddha,Chandra Ghosh, Subhash,Kundu, Susmita,Panda, Asit Baran
p. 102134 - 102142
(2015/12/11)

The synthesis of tetrazoles in nanometer aqueous micelles at room temperature
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
p. 436 - 441
(2014/01/23)

The Synthesis of Tetrazoles in Nanometer Aqueous Micelles at Room Temperature
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
p. 436 - 441
(2015/10/05)

Hierarchically porous AlPO-5-based microspheres as heterogeneous catalysts for the synthesis of 5-substituted 1H-tetrazoles via [3+2] cycloaddition
The research on the heterogeneous catalytic synthesis of tetrazoles has attracted great attention. In this paper, a tungsten atom-containing AlPO-5 microporous molecular sieve (termed as WAlPO-5) was designed and synthesized by the incorporation of tungst
Kong, Dan,Liu, Yanyan,Zhang, Juan,Li, Hongbian,Wang, Xiangyu,Liu, Guangyu,Li, Baojun,Xu, Zheng
p. 3078 - 3083
(2014/07/07)

Nano TiO2/SO42- as a heterogeneous solid acid catalyst for the synthesis of 5-substited-1 H-tetrazoles
An efficient and economical protocol for the synthesis of 5-substituted-1H-tetrazoles from various nitriles and sodium azide is reported using nano TiO2/SO42+ as an effective heterogeneous catalyst.A wide variety of aryl nitriles underwent [3 + 2] cycloaddition to afford tetrazoles in good to excellent yields.
Hosseini-Sarvari, Mona,Najafvand-Derikvandi, Sepideh
p. 1007 - 1012
(2015/01/09)

Synthesis, characterization and catalytic activity of graphene oxide/ZnO nanocomposites
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
p. 36713 - 36720
(2014/12/09)

PH-dependent synthesis of a cadmium coordination compound from a compound based on Hpytz ligand [Hpytz = 5-(4-pyridyl)tetrazole]
Reactions of CdSO4·6H2O and Hpytz [Hpytz = 5-(4-pyridyl)tetrazole] under high pH values produced a known compound, [Cd(pytz)2(H2O)4]·2H2O (1), which can be used to prepare [Cd(Hpytz)(SO4)(H2O)2] (2) by adjusting the pH to a lower level using sulfuric acid
Zou, Jian Hua,Wu, He,Zhu, Da Liang,Tian, He,Zhang, Ping,Zhao, Li Yang,Ruan, Zhi Wei,Xie, Jian,Li, Qiao Yun,Yang, Gao Wen
p. 3444 - 3453
(2015/10/20)

A Ratiometric Tetrazolylpyridine-Based "turn-On" Fluorescent Chemosensor for Zinc(II) Ion in Aqueous Media
The highly selective ratiometric "turn-on" fluorescent sensing of Zn2+ ion involving 2-(1H-tetrazole-5-yl)pyridine (2PT) in aqueous medium is reported, which is not observed when other metal ions are present. Upon 2PT binding selectively with Zn2+ ion, a fluorescence enhancement is observed that is attributed to an enhancement of localized emission and suppression of excited-state intramolecular proton transfer. The described sensing system involving 2PT is also successfully applied to the detection of Zn2+ ion in real samples with a detection limit of 7.5×10-7 M.
Kaleeswaran, Palanichamy,Azath, Ismail Abulkalam,Tharmaraj, Vairaperumal,Pitchumani, Kasi
p. 1361 - 1366
(2016/02/18)