5378-52-9Relevant academic research and scientific papers
Removal of the Cd(II), Ni(II), and Pb(II) ions via their complexation with the uric acid-based adsorbent and use of the corresponding Cd-complex for the synthesis of tetrazoles
Ahmadi, Sharareh,Ariannezhad, Maryam,Habibi, Davood,Heydari, Somayyeh,Jafari, Ali
, (2021/11/22)
The magnetic supported uric acid-based compound (Fe3O4@SiO2@CPTMS@UA) was prepared, characterized and used as a capable adsorbent for removal of the Cd(II), Ni(II) and Pb(II) ions from aqueous solution. The Freundlich and Langmuir adsorption isotherms have been used to evaluate the adsorption behaviors. The high correlation coefficient of the Langmuir model (R+2 > 0.99) reveals that the Langmuir model offers the better coordination with the experimental results and so the model of adsorption of Cd2+, Ni2+, and Pb2+ on the adsorbent is more compatible with the Langmuir model, and the maximum adsorption capacity for the Cd, Ni, and Pb ions are about 285.7, 45.06 and 145.09 mg/g. Then, the corresponding Cd-complex (Fe3O4@SiO2@CPTMS@ UA@Cd) was also prepared, characterized and applied as an efficient heterogeneous nano-catalyst for the synthesis of diverse tetrazoles.
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.
The anchoring of a Cu(ii)-salophen complex on magnetic mesoporous cellulose nanofibers: green synthesis and an investigation of its catalytic role in tetrazole reactions through a facile one-pot route
Bagherzade, Ghodsieh,Ghamari kargar, Pouya
, p. 19203 - 19220 (2021/06/03)
Today, most synthetic methods are aimed at carrying out reactions under more efficient conditions and the realization of the twelve principles of green chemistry. Due to the importance and widespread applications of tetrazoles in various industries, especially in the field of pharmaceutical chemistry, and the expansion of the use of nanocatalysts in the preparation of valuable chemical reaction products, we decided to use an (Fe3O4@NFC@NSalophCu)CO2H nanocatalyst in this project. In this study, the synthesis of the nanocatalyst (Fe3O4@NFC@NSalophCu)CO2H was explained in a step-by-step manner. Confirmation of the structure was obtained based on FT-IR, EDX, FE-SEM, TEM, XRD, VSM, DLS, TGA, H-NMR, and CHNO analyses. The catalyst was applied to the synthesis of 5-substituted-1H-tetrazole and 1-substituted-1H-tetrazole derivatives through multi-component reactions (MCRs), and the performance was assessed. With advances in science and technology and increasing environmental pollution, the use of reagents and methods that are less dangerous for the environment has received much attention. Therefore, following green chemistry principles, with the help of the (Fe3O4@NFC@NSalophCu)CO2H salen complex as a nanocatalyst that is recyclable, cheap, safe, and available, the use of water as a green solvent, and reduced reaction times, the synthesis of tetrazoles can be achieved.
Efficient reduction of nitro compounds and domino preparation of 1-substituted-1H-1,2,3,4-tetrazoles by Pd(ii)-polysalophen coated magnetite NPs as a robust versatile nanocomposite
Xu, DaPeng,Xiong, Meilu,Kazemnejadi, Milad
, p. 12484 - 12499 (2021/04/14)
A new, versatile, and green methodology has been developed for the efficient NaBH4-reduction of nitroarenes as well as the domino/reduction MCR preparation of 1-substituted-1H-1,2,3,4-tetrazoles using Pd(ii)-polysalophen coated magnetite NPs as an efficient heterogeneous magnetically recyclable nanocatalyst. Polysalophen was firstly prepared based on a triazine framework with a high degree of polymerization, then coordinated to Pd ions and, finally, the resulting hybrid was immobilized on magnetite NPs. The catalyst was characterized by various instrumental and analytical methods, including GPC, DLS, N2adsorption-desorption, TGA, VSM, TEM, HRTEM, EDX, XPS, XRD, and ICP analyses. The catalyst possesses dual-functionality including the reduction of nitroarenes and the construction of tetrazole rings all in one stepviaa domino protocol. High to excellent yields were obtained for both nitro reduction and the direct preparation of 1-substituted-1H-1,2,3,4-tetrazoles from nitro compounds. Insight into the mechanism was conducted by XPSin situas well as DLSin situalong with several control experiments. Recyclability of the catalyst was studied for 6 consecutive runs along with metal leaching measurements in each cycle.
Polymer-Supported Fe-Phthalocyanine Derived Heterogeneous Photo-Catalyst for the Synthesis of Tetrazoles Under Visible Light Irradiation
Khajone, Vijay Baburao,Balinge, Kamlesh Rudreshwar,Bhagat, Pundlik Rambhau
, p. 1948 - 1960 (2020/11/23)
Abstract: Herein, a polymer supported Fe-Phthalocyanine entangled with carboxyl functionalized benzimidazolium moiety (PSFePcCFBM) explored as heterogenous photocatalyst, for regioselective synthesis of 1H-tetrazoles from sodium azide and other affordable
Copper coordinated-poly(α-amino acid) decorated on magnetite graphene oxide as an efficient heterogeneous magnetically recoverable catalyst for the selective synthesis of 5- and 1-substituted tetrazoles from various sources: A comparative study
Kazemnejadi, Milad,Mahmoudi, Boshra,Sharafi, Zeinab,Nasseri, Mohammad A.,Allahresani, Ali,Esmaeilpour, Mohsen
, (2019/12/15)
In this work, poly(α-amino acid)-Cu(II) complex immobilized on magnetite graphene oxide (GO/Fe3O4?PAA-Cu-complex) was prepared via a multistep synthesis and employed as an efficient, heterogeneous, magnetically recyclable nanocatalyst for one-pot, three component synthesis of 5- and 1-substituted tetrazoles using different substrates including benzaldehydes, benzonitriles, and anilines in mild conditions. The different approaches were mechanically investigated and compared. The catalyst was fully characterized by Fourier transform infrared (FTIR), thermogravimetric analysis (TGA), X-ray diffraction (XRD), vibrating sample magnetometer (VSM), energy dispersive X-ray spectroscopy (EDX), inductively coupled plasma (ICP), FE-SEM and TEM analyses. The magnetic nanocatalyst could be readily separated from the reaction mixture by an external magnet and reused for several times without significant loss of catalytic activity. Also, the spectroscopic analysis revealed the stability and durability of the catalyst. Finally, the chemoselectivity of the method was investigated by the various combinations of aldehyde, nitrile, and oxime.
Fe3O4?Hydrotalcite-NH2-CoII NPs: A novel and extremely effective heterogeneous magnetic nanocatalyst for synthesis of the 1-substituted 1H-1, 2, 3, 4-tetrazoles
Esmaeli-nasrabadi, Farzaneh,Salimi, Mehri,Sandaroos, Reza
, (2020/10/27)
In this study, we present a versatile and easy procedure for modifying a ferrite nanoparticles so step by step. A new nanocatalyst was prepared via CoII immobilized onto an aminated ferrite nanoparticles (Fe3O4?HT?AEPH2-CoII). The catalyst was fully characterized by FT-IR, EDX, FE-SEM, TGA, XRD, and VSM analyses. In the preparation of 1-substituted-1-H-tetrazole, the corresponding nanocatalyst shown great catalytic activity. The reaction contains expeditious reusable catalyst (Fe3O4?AEPH2-CoII) that promotes condensation between sodium azide, triethyl ortho-formate, and diversity of heterocyclic/aromatic amines. Also, an environmentally toxic solvent was eliminated. A significant improvement in the synthetic efficacy (95%, yield) was obtained by this new sustainable and eco-friendly protocol as well as high purity. The current procedure as a green protocol offers benefits including a simple operational procedure, an excellent yield of products, mild reaction conditions, minimum chemical wastes, short reaction time, and easy catalyst synthesis. Without any significant reduction in the catalytic performance, up to four recyclability cycles of the catalyst were obtained. The optimization results suggest that the best condition in the preparation of tetrazole derivatives is 0.005 g of the Fe3O4?HT?AEPH2-CoII catalyst where H2O is the solvent at 90 °C. The proposed protocol could be applied on a wider scope of the substrate (i.e., electron-deficient and electron-rich).
Green synthesis of the 1-substituted 1H-1, 2, 3, 4-tetrazoles over bifunctional catalyst based on copper intercalated into Mg/Al hydrotalcite modified magnetite nanoparticles
Salimi, Mehri,Zamanpour, Azadeh
, (2020/05/16)
An effective one-pot, convenient process for the synthesis of 1- substituted 1H-tetrazoles from triethyl orthoformate, amines, and sodium azide is described using copper (II) doped and immobilized on functionalized magnetic hydrotalcite (Fe3O4/HT-NH2 CuII) as a novel recyclable catalyst. The application of this catalyst allows the synthesis of a variety of tetrazoles in good to excellent yields in water. The new catalyst was characterized using Fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD), scanning electron microscopy (SEM), energy-dispersive X-ray spectroscopy (EDX), thermogravimetric analysis (TGA), vibration sample magnetometry (VSM) and inductively coupled plasma analysis (ICP-OES). This new procedure offers several advantages such as short operational simplicity, practicability, and applicability to various substrates and the absence of any tedious workup or purification. The loading amount of CuII (doped and immobilized) on functionalized magnetic hydrotalcite was indicated to be 4.66 mmol g?1, obtained from the ICP-OES analysis. Also, the excellent catalytic performance, thermal stability, and separation of the catalyst make it an excellent heterogeneous system and a useful alternative to other heterogeneous catalysts. Also, the catalyst could be magnetically separated and reused six times without significant loss of catalytic activity.
Cyanide-Free Synthesis of Air Stable N-Substituted Li and K Cyanamide Salts from Tetrazoles. Applications toward the Synthesis of Primary and Secondary Cyanamides as Precursors to Amidines
Duchamp, Edouard,Hanessian, Stephen
supporting information, p. 8487 - 8491 (2020/11/12)
A practical two-step synthesis of N,N′-disubstituted cyanamides consists in the low-temperature metalation of N-substituted 5H-tetrazoles that undergo spontaneous cycloreversion at 0 °C releasing dinitrogen, and forming N-metalated cyanamides that can be reacted in situ with a variety of electrophiles. Remarkably, the N-substituted Li and K cyanamides are air stable white solids at room temperature. Addition of lithium organometallics to the N,N′-disubstituted cyanamides provides a new method for accessing N,N′-disubstituted amidines.
Chemoselective reduction of isothiocyanates to thioformamides mediated by the Schwartz reagent
De La Vega-Hernández, Karen,Senatore, Raffaele,Miele, Margherita,Urban, Ernst,Holzer, Wolfgang,Pace, Vittorio
supporting information, p. 1970 - 1978 (2019/02/20)
Thioformamides are easily prepared-under full chemocontrol-through the partial reduction of isothiocyanates with the in situ generated Schwartz reagent. The high electrophilicity of the starting materials enables the straightforward addition of the hydride ion, thus constituting a reliable and high-yielding method for obtaining variously functionalized thioformamides. Sensitive chemical groups to the reduction conditions such as nitro, ester, alkene, azo, azide and keto groups do not interfere with the chemoselectivity of the process. Moreover, the stereochemical information embodied in the starting material is fully retained in the final products. The synthetic potential of the selected thioformamide template is also briefly discussed.
