14389-10-7Relevant articles and documents
A novel approach for the synthesis of 5-substituted-1H-tetrazoles
Akhlaghinia, Batool,Rezazadeh, Soodabeh
, p. 2197 - 2203 (2012)
A series of 5-substituted-1H-tetrazoles (RCN4H) have been synthesized by cycloaddition reaction of different aryl and alkyl nitriles with sodium azide in DMSO using CuSO4?5H2O as catalyst. A wide variety of aryl nitriles underwent [3+2] cycloaddition to afford tetrazoles under mild reaction conditions in good to excellent yields. The catalyst used is readily available and environmentally friendly. Short reaction times, good to excellent yields, safe process and simple workup make this method an attractive and useful contribution to present organic synthesis of 5-substituted-1H- tetrazoles. ?2012 Sociedade Brasileira de Qui?mica.
Copper and nickel immobilized on cytosine@MCM-41: as highly efficient, reusable and organic–inorganic hybrid nanocatalysts for the homoselective synthesis of tetrazoles and pyranopyrazoles
Nikoorazm, Mohsen,Tahmasbi, Bahman,Gholami, Shahab,Moradi, Parisa
, (2020)
In this work, a green approach is reported for efficient synthesis of biologically active tetrazole and pyranopyrazole derivatives in the presence of Cu-Cytosine@MCM-41 and Ni-Cytosine@MCM-41 (copper (II) and nickel (II) catalyst on the modified MCM-41 us
Clay-catalyzed synthesis of 5-substituent 1-H-tetrazoles
Chermahini, Alireza Najafi,Teimouri, Abbas,Momenbeik, Fariborz,Zarei, Amin,Dalirnasab, Zeinab,Ghaedi, Aseyeh,Roosta, Mostafa
, p. 913 - 922 (2010)
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.
Cu(ii) immobilized on aminated epichlorohydrin activated silica (CAES): As a new, green and efficient nanocatalyst for preparation of 5-substituted-1H-tetrazoles
Razavi, Nasrin,Akhlaghinia, Batool
, p. 12372 - 12381 (2015)
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.
Fabricated copper catalyst on biochar nanoparticles for the synthesis of tetrazoles as antimicrobial agents
Moradi, Parisa,Hajjami, Maryam,Tahmasbi, Bahman
, (2020)
Biochar is a carbon-rich solid which its surface was covered by high density of carbonyl, hydroxyl and carboxylic acid functional groups. In this work, biochar nanoparticles were prepared from pyrolysis of chicken manure and further a new copper catalyst
The first report on the eco-friendly synthesis of 5-substituted 1: H -tetrazoles in PEG catalyzed by Cu(ii) immobilized on Fe3O4@SiO2@l-arginine as a novel, recyclable and non-corrosive catalyst
Ghorbani-Choghamarani, Arash,Shiri, Lotfi,Azadi, Gouhar
, p. 32653 - 32660 (2016)
Cu(ii) immobilized on Fe3O4@SiO2@l-aginine as a novel, inexpensive and non-corrosive nanostructured compound catalyzed the cycloaddition reaction of various organic nitriles with sodium azide. This combination leads to obt
Zeolite and sulfated zirconia as catalysts for the synthesis of 5-substituted 1H-tetrazoles via [2+3] cycloaddition of nitriles and sodium azide
Teimouri, Abbas,Najafi Chermahini, Alireza
, p. 2606 - 2610 (2011)
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.
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
Jahanshahi, Roya,Akhlaghinia, Batool
, p. 104087 - 104094 (2015)
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.
Nano TiO2/SO42- as a heterogeneous solid acid catalyst for the synthesis of 5-substited-1 H-tetrazoles
Hosseini-Sarvari, Mona,Najafvand-Derikvandi, Sepideh
, p. 1007 - 1012 (2014)
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.
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.
, p. 292 - 298 (2020)
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.
Boehmite@SiO2@ Tris (hydroxymethyl)aminomethane-Cu(I): a novel, highly efficient and reusable nanocatalyst for the C-C bond formation and the synthesis of 5-substituted 1H-tetrazoles in green media
Ghorbani-Choghamarani, Arash,Aghavandi, Hamid,Mohammadi, Masoud
, (2020)
In this work, a versatile protocol was introduced for the preparation of a new Cu(I) supported complex on Silica supported boehmite nanoparticles (Boehmite@SiO2@Tris-Cu(I)). The structure of the catalyst was comprehensively characterized using
Kinetics of azidation of isomeric benzenedicarbonitriles
Popova,Pavlyukova,Popov,Ostrovskii,Trifonov
, p. 890 - 894 (2009)
Rate constants and activation parameters of two-step azidation of isomeric dicyanobenzenes with dimethylammonium azide in DMF at 70-100°C were determined. Tetrazole rings are formed from cyano groups in dicyanobenzenes in a stepwise mode following the 1,3
Cu-MCM-41 nanoparticles: An efficient catalyst for the synthesis of 5-substituted 1H-tetrazoles via [3+2] cycloaddition reaction of nitriles and sodium azide
Abdollahi-Alibeik, Mohammad,Moaddeli, Ali
, p. 93 - 99 (2016)
[3 + 2] cycloaddition reaction of various types of nitriles and sodium azide (NaN 3) were studied in the presence of nano-sized Cu-MCM-41 as an efficient recoverable heterogeneous catalyst. Nano-sized Cu-MCM-41 mesoporous molecular sieves with various Si/Cu molar ratios were synthesized by direct insertion of metal ions at room temperature. The textural properties of the materials have been studied by means of XRD, FTIR, SEM and TEM techniques. Catalytic behavior of Cu-MCM-41 was also investigated by pyridine absorption and potentiometric titration. The reactions data verified characterization results and show that Cu-MCM-41 with Si/Cu molar ratio of 20 has considerably better catalytic activity compared to the other molar ratios. To investigate reusability, the catalyst was recovered by simple filtration and reused for several cycles with consistent activity.
Oxidation/ MCR domino protocol for direct transformation of methyl benzene, alcohol, and nitro compounds to the corresponding tetrazole using a three-functional redox catalytic system bearing TEMPO/Co(III)-porphyrin/ Ni(II) complex
Mahmoudi, Boshra,Rostami, Amin,Kazemnejadi, Milad,Hamah-Ameen, Baram Ahmed
, (2020/12/21)
A redox catalytic system for oxidation-reduction reactions and the domino preparation of tetrazole compounds from nitro and alcohol precursors was designed, prepared and characterized by UV–vis, GPC, TGA, XRD, EDX, XPS, VSM, FE-SEM, TEM, DLS, BET, NMR, and ICP analyses. The catalyst was prepared via several successive steps by demetalation of chlorophyll b, copolymerization with acrylated TEMPO monomers, complexation with Ni and Co metals (In two different steps), then immobilized on magnetic nanoparticles. The presence of three functional groups including TEMPO, coordinated cobalt, and coordinated nickel in the catalyst, allowed the oxidation of various types of alcohols, alkyl benzenes as well as the reduction of nitro compounds by a single catalyst. All reactions yielded up to 97 % selectivity for oxidation and reduction reactions. Next, the ability of the catalyst to successfully convert alcohol, methyl benzenes and nitro to their corresponding tetrazoles was studied.
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.
