- Salen complex of Cu(II) supported on superparamagnetic Fe3O 4@SiO2 nanoparticles: An efficient and recyclable catalyst for synthesis of 1- and 5-substituted 1H-tetrazoles
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An efficient and general method has been developed for synthesis of 1- and 5-substituted 1H-tetrazoles from nitriles and amines using magnetite nanoparticles immobilized Salen Cu(II) as an efficient and recyclable catalyst. The structural and magnetic properties of functionalized magnetic silica are identified by transmission electron microscopy (TEM), scanning electron microscopy (SEM) and vibrating sample magnetometer (VSM) instruments. NMR, FT-IR, elemental analysis and XRD were also used for identification of these structures. Nanocatalyst can be easily recovered by a magnetic field and reused for subsequent reactions for at least 7 times with less deterioration in catalytic activity.
- Dehghani, Farzaneh,Sardarian, Ali Reza,Esmaeilpour, Mohsen
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- One-pot synthesis of 1- and 5-substituted 1H-tetrazoles using 1,4-dihydroxyanthraquinone–copper(II) supported on superparamagnetic Fe3O4@SiO2 magnetic porous nanospheres as a recyclable catalyst
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An effective one-pot, convenient process for the synthesis of 1- and 5-substituted 1H-tetrazoles from nitriles and amines is described using1,4-dihydroxyanthraquinone–copper(II) supported on Fe3O4@SiO2 magnetic porous nanospheres as a novel recyclable catalyst. The application of this catalyst allows the synthesis of a variety of tetrazoles in good to excellent yields. The preparation of the magnetic nanocatalyst with core–shell structure is presented by using nano-Fe3O4 as the core, tetraethoxysilane as the silica source and poly(vinyl alcohol) as the surfactant, and then Fe3O4@SiO2 was coated with 1,4-dihydroxyanthraquinone–copper(II) nanoparticles. The new catalyst was characterized using Fourier transform infrared spectroscopy, X-ray diffraction, transmission electron microscopy, field emission scanning electron microscopy, dynamic light scattering, thermogravimetric analysis, vibration sample magnetometry, X-ray photoelectron spectroscopy, nitrogen adsorption–desorption isotherm analysis and inductively coupled plasma analysis. This new procedure offers several advantages such as short reaction times, excellent yields, operational simplicity, practicability and applicability to various substrates and absence of any tedious workup or purification. In addition, the excellent catalytic performance, thermal stability and separation of the catalyst make it a good 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. Copyright
- Esmaeilpour, Mohsen,Javidi, Jaber,Zahmatkesh, Saeed
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- 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
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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.
- Kazemnejadi, Milad,Mahmoudi, Boshra,Sharafi, Zeinab,Nasseri, Mohammad A.,Allahresani, Ali,Esmaeilpour, Mohsen
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- SYNTHESIS OF 1-SUBSTITUTED TETRAZOLES BY HETEROCYCLIZATION OF PRIMARY AMINES, ORTHOFORMIC ESTER, AND SODIUM AZIDE
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It has been shown that the reaction of heterocyclization of primary amines with orthoformic acid and sodium azide in acetic acid has a rather general character and is a convenient method for the synthesis of 1-substituted tetrazoles.On the basis of experimental data, a probable reaction mechanism is proposed.
- Gaponik, P. N.,Karavai, V. P.,Grigor'ev, Yu. V.
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- One pot three component solvent free synthesis of N-substituted tetrazoles using RuO2 /MMT catalyst
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A facile, one-pot three component catalytic method is developed for the synthesis of N-substituted tetrazole using RuO2/MMT nanocomposite. It is characterized with low and wide angle XRD which suggests that RuO2 nanoparticles are evenly dispersed on the surface of MMT while FESEM images indicate a spherical morphology having size in the range of 40-50 nm. The catalytic efficiency is evaluated for three component one-pot synthesis of the tetrazole using various amine, sodium azide and triethyl-ortho-formate under solvent free condition. This strategy has resulted in good to excellent yields (84 – 97percent) of N-substituted tetrazoles within moderate reaction time. Moreover, the catalyst possesses excellent reusability up to five cycles with only 5percent decrease in the yield of tetrazole after 5th cycle. The beneficial catalytic activity of the bifunctional nanocomposite is attributed to the uniformly dispersed RuO2 nanoparticles on the surface of MMT where RuO2 site is responsible for coordination of isocyanide intermediate while strong acidic character of MMT induces condensation and cyclization steps in a synergic manner. Thus, it can be argued that RuO2/MMT nanocomposite possesses potential applications for Multi Component Reactions (MCR) in terms of efficient and sustainable manner.
- Chikate, Rajeev C.,Pawar, Hari R.
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- Facile synthesis of 1- and 5-substituted 1H-tetrazoles catalyzed by recyclable ligand complex of copper(II) supported on superparamagnetic Fe 3O4@SiO2 nanoparticles
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We report a new method for preparing functionalized superparamagnetic Fe3O4@SiO2 possessing high saturation magnetization. Magnetite particles were prepared by simple co-precipitation method in aqueous medium, and then Fe3O4@SiO2 nanosphere was synthesized by using nano Fe3O4 as the core, TEOS as the silica source and polyethylene glycol (PEG 1000) as the surfactant. Then, the silica-coated Fe3O4 nanoparticles were covered with ligand complex of Cu(II). The functionalized magnetic core-shell nanoparticles (MNPs) were investigated by Fourier transform infrared spectroscopy, transmission electron microscopy, scanning electron microscopy, X-ray diffraction, thermogravimetric analysis, dynamic light scattering and N2 adsorption/desorption. Also, its Cu content was determined by inductively coupled plasma (ICP) analyzer. Then, the immobilized copper complex was used as an efficient catalyst for synthesis of 1- and 5-substituted 1H-tetrazoles from nitriles and amines in good to excellent yields. The results show that the supported catalyst could be conveniently recovered through the use of an external magnetic field and reused for subsequent reactions for at least 6 times with less deterioration in catalytic activity.
- Esmaeilpour, Mohsen,Javidi, Jaber,Nowroozi Dodeji, Fatemeh,Mokhtari Abarghoui, Mehdi
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- 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
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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.
- Bagherzade, Ghodsieh,Ghamari kargar, Pouya
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- Synthesis of 1-substituted tetrazoles via the acid-catalyzed [3+2] cycloaddition between isocyanides and trimethylsilyl azide
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1-Substituted tetrazoles were synthesized via the [3+2] cycloaddition between isocyanides and trimethylsilyl azide in the presence of an acid catalyst and MeOH. Various 1-substituted tetrazoles were obtained in good to high yields. The reaction probably p
- Jin, Tienan,Kamijo, Shin,Yamamoto, Yoshinori
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- 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
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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.
- Ahmadi, Sharareh,Ariannezhad, Maryam,Habibi, Davood,Heydari, Somayyeh,Jafari, Ali
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- Practical synthesis of tetrazoles from amides and phosphorazidates in the presence of aromatic bases
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Tetrazoles were effectively synthesized from amides using diphenyl phosphorazidate or bis(p-nitrophenyl) phosphorazidate in the presence of aromatic bases. Various amides underwent the proposed cycloaddition reaction to provide the corresponding tetrazoles. Studies on the racemization of chiral substrates were also performed. Overall, the proposed synthesis method enables the preparation of 1,5-disubstituted and 1-substituted tetrazoles, and 5-substituted 1H-tetrazoles without using toxic or explosive reagents.
- Ishihara, Kotaro,Ishihara, Kazuki,Tanaka, Yota,Shioiri, Takayuki,Matsugi, Masato
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supporting information
(2022/02/02)
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- Polymer-Supported Fe-Phthalocyanine Derived Heterogeneous Photo-Catalyst for the Synthesis of Tetrazoles Under Visible Light Irradiation
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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
- Khajone, Vijay Baburao,Balinge, Kamlesh Rudreshwar,Bhagat, Pundlik Rambhau
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p. 1948 - 1960
(2020/11/23)
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- 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
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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).
- Esmaeli-nasrabadi, Farzaneh,Salimi, Mehri,Sandaroos, Reza
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- 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
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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.
- Salimi, Mehri,Zamanpour, Azadeh
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- Synthesis of Tetrazoles from Amines Mediated by New Copper Nanocatalyst
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New copper nanocatalyst was prepared by coating Fe3O4 magnetic nanoparticles with tetraethyl orthosilicate (TEOS), followed by functionalization with 3-chloropropyl(trimethoxy)silane and 4H-1,2,4-tri-azol-4-amine and complexation with copper(II) chloride. The new catalyst was characterized by various spectroscopic methods and was successfully used in the synthesis of 1-aryl-1H-tetrazoles by reaction of aromatic amines with sodium azide and triethyl orthoformate under solvent-free conditions at 100°C.
- Ariannezhad,Habibi,Heydari
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p. 1591 - 1597
(2019/12/28)
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- One-pot green synthesis of Cu/bone nanocomposite and its catalytic activity in the synthesis of 1-substituted 1H-1,2,3,4-tetrazoles and reduction of hazardous pollutants
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In this work, a simple and green method is reported for the biosynthesis of Cu/bone nanocomposite using Cordyline fruticosa extract as a stabilizer and reductant. Animal bone was used as a natural support to prevent the accumulation of Cu nanoparticles. The catalytic activity of Cu/bone nanocomposite was assessed in the synthesis of 1-substituted 1H-1,2,3,4-tetrazoles and reduction of various organic dyes, including 4-nitrophenol (4-NP), nigrosin (NS), congo red (CR) and methylene blue (MB). The best catalytic performance in the synthesis of 1-substituted tetrazoles was achieved using 0.05?g of Cu/bone nanocomposite at 120°C. In addition, under optimal conditions, the absorption bands corresponding to 4-NP, CR, NS and MB completely disappeared after about 6?min, 3?min, 50?s and 7?s, respectively. The biosynthesis protocol used in the preparation of Cu/bone nanocomposite offers a very attractive area for further research.
- Maham, Mehdi,Nasrollahzadeh, Mahmoud
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- Synthesis of Tetrazoles Catalyzed by Novel Cobalt Magnetic Nanoparticles
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A novel magnetic Co nanoparticle catalyst was prepared by coating Fe304magnetic nanoparticles with tetraethyl orthosilicate functionalized with (3-chloropropyl)trimethoxysilane and 2-amino-5-mercapto-1,3,4-thiadiazole ligands followed by complexation with Co(OAc)4. The catalyst was then characterized and applied for the synthesis of various tetrazoles by the reactions of amines with sodium azide and triethyl orthoformate in solvent-free conditions at 100°C.
- Sarrafioun,Jamehbozorgi,Ramezani
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p. 1777 - 1784
(2020/01/11)
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- Preparation of Fe3O4@5,10-dihydropyrido[2,3-b]quinoxaline-7,8-diol copper complex: A capable nanocatalyst for the green synthesis of 1-substituted 1H-tetrazoles
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Fe3O4 magnetic nanoparticles functionalized with 5,10-dihydropyrido[2,3-b]quinoxaline-7,8-diol were synthesized as was their complex with copper as a novel nanomagnetic iron oxide catalyst via a simple and green method, and characterized using various techniques. The capability of the catalyst was evaluated in the one-pot three-component synthesis of different tetrazoles, which showed very good results. Mild reaction conditions, good reusability and simple magnetic work-up make this methodology interesting for the efficient synthesis of tetrazoles.
- Habibi, Davood,Pakravan, Narges,Arabi, Ameneh,Kaboudvand, Zahra
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- Azasydnone-novel "green" building block for designing high energetic compounds
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The discovery of novel explosophoric building blocks for the construction of energetic compounds is extremely rare. Here, based on the comparative experimental properties and computational analysis of compounds where nitroaryl backbones were bonded with various nitrogen/oxygen-rich groups, it is shown that compounds having the azasydnone group possess higher density, detonation performance and thermal stability than their corresponding nitro, azido and tetrazole-analogs. All of these properties, as well as the oxygen balanced content of the "green" nitrogen rich endothermic unit make them an attractive explosophoric building block in the field of energetic materials chemistry.
- Dalinger, Igor L.,Serushkina, Olga V.,Muravyev, Nikita V.,Meerov, Dmitry B.,Miroshnichenko, Evgeniy A.,Kon'Kova, Tatyana S.,Suponitsky, Kyrill Yu.,Vener, Mikhail V.,Sheremetev, Aleksei B.
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p. 18669 - 18676
(2018/10/15)
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- Visible-light driven regioselective synthesis of 1H-tetrazoles from aldehydes through isocyanide-based [3 + 2] cycloaddition
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A novel and green Co@g-C3N4 catalyzed visible light driven direct regioselective synthesis of 1H-tetrazoles directly from various aldehydes and sodium azide is reported. Herein, NaN3 not only behaves as a three-nitrogen do
- Verma, Fooleswar,Sahu, Anjumala,Singh, Puneet K.,Rai, Ankita,Singh, Manorama,Rai, Vijai K.
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supporting information
p. 3783 - 3789
(2018/08/21)
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- CATHEPSIN K INHIBITOR AND APPLICATION THEREOF
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The invention relates to capthepsin K inhibitors and uses thereof, specifically relates to a class of compounds having the formula (I) which are used for treating or preventing cathepsin dependent diseases or conditions, specifically, wherein the cathepsin is capthepsin K. The compounds and compositions thereof can be used as bone resorption inhibitors for the treatment of associated diseases.
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Paragraph 0312
(2018/07/29)
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- Application of the Fe3O4@1,10-phenanthroline-5,6-diol@Mn nano-catalyst for the green synthesis of tetrazoles and its biological performance
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The Fe3O4 magnetic particles were modified with 1,10-phenanthroline-5,6-diol (Phen) and the related Mn complex (Fe3O4@Phen@Mn) synthesized as a heterogeneous catalyst to be used for the one-pot three-component synthesis of various tetrazoles. The catalysts were characterized by several methods, such as the elemental analysis, FT-IR, X-ray powder diffraction, dispersive X-ray spectroscopy, scanning electron microscopy, transmission electron microscopy, dynamic light scattering, thermogravimetric-differential thermal analysis, vibrating sample magnetometer and X-ray photoelectron spectroscopy. In addition, the antioxidant and antibacterial activities of the catalyst and its Phen ligand were in vitro screened with 2,2-diphenyl-1-picrylhydrazyl by free radical scavenging methods. Results showed that the synthesized compounds possess strong antioxidant activity (IC50; 0.172 ± 0.005 mg ml?1) as well as a good antibacterial potential in comparison to standards.
- Habibi, Davood,Heydari, Somayyeh,Gil, Antonio,Afsharfarnia, Mina,Faraji, Alireza,Karamian, Roya,Asadbegy, Mostafa
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- Synthetic manifestation of nitro substituted tetrazole-N-(hetero)aryl derivatives and energetic studies
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A workable cost-efficient synthetic method for the construction of nitro substituted tetrazole-N-aryl/heteroaryl derivatives is discussed here. The energetic functional groups-NO2,-NHNO2 and-N3 are reliably inserted into the molecular backbone, making the tetrazole-N-aryl derivatives highly energetic and insensitive to heat and impact. For example, the tetrazole derivatives 7 and 8, bearing a-NO2 or a-NHNO2 group, exhibit energetic properties close to RDX, but with enhanced insensitivity. Most of the synthesized compounds show exothermic decomposition and are consequently useful for energetic material applications.
- Kommu, Nagarjuna,Balaraju,Ghule, Vikas D.,Sahoo, Akhila K.
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supporting information
p. 7366 - 7371
(2017/04/26)
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- 2-aminoethanesulfonic acid immobilized on epichlorohydrin functionalized Fe3O4@WO3 (Fe3O4@WO3-EAE-SO3H): A novel magnetically recyclable heterogeneous nanocatalyst for the green one-pot synthesis of 1-substituted-1H-1, 2, 3, 4-tetrazoles in water
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In this research 2-aminoethanesulfonic acid immobilized on epichlorohydrin functionalized Fe3O4@WO3 (Fe3O4@WO3- EAE-SO3H) has been introduced as a novel and efficient magnetic nanocatalyst for appropriate and rapid synthesis of 1-substituted-1H-1, 2, 3, 4-tetrazoles. This new nanocatalyst was then characterized using FT-IR, XRD, TEM, EDS, TGA, FE-SEM, CHNS and VSM techniques. The above experimental results allowed determination of the composition of Fe3O4@WO3-EAE-SO3H and clearly revealed that the nanoparticles are spherical in shape with particle size in the range of 723nm and superparamagnetic behavior. Fe3O4@WO3- EAE-SO3H as an excellent replacement for Br?nsted acids was shown to be highly efficient in the rapid preparation of 1- substituted-1H-1, 2, 3, 4-tetrazoles through the cyclization reaction of various primary amines, triethyl orthoformate and 1- butyl-3-methylimidazolium azide ([bmim][N3]). Compared with conventional methods, the present protocol has considerable advantages such as short reaction time, mild reaction conditions, easy work-up, pure products with high yields, catalyst recovery using an external magnet and reuse of the catalyst several times without noticeable deterioration in catalytic activity. In addition to the aforementioned favourable properties, the remarkable feature of the present protocol is the use of water as environmentally benign solvent, which eliminates the use of toxic solvent.
- Ghasemzadeh, Maryam Sadat,Akhlaghinia, Batool
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p. 1119 - 1128
(2017/10/25)
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- IMINOSUGARS USEFUL FOR THE TREATMENT OF VIRAL DISEASES
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Formula IA, ad their use for treating viral infections.
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Page/Page column 62
(2016/06/01)
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- Cross-linked poly (4-vinylpyridine) supported azide ion as a versatile and recyclable polymeric reagent for synthesis of 1-substituted-1H-1,2,3,4- tetrazoles
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Cross-linked poly (4-vinylpyridine) supported azide ion, [P 4-VP]N3, is easily prepared and used as an efficient polymeric reagent for synthesis of 1-substituted-1H-1,2,3,4-tetrazoles via condensation reaction of azide ion, primary aromatic amines, and triethyl orthoformate in glacial acetic acid. After optimization of the reaction conditions, a wide variety of primary aromatic amines were also subjected to preparation of the corresponding 1-aryl-1 H-1,2,3,4- tetrazoles using [P 4-VP]N3 under heterogeneous conditions. In this method, the reaction times were very short and the isolated yields were excellent (90-98 %). 1-Aryl-1H-1,2,3,4- tetrazole products were characterized by Fourier transform infrared (FT-IR) and some of them were also characterized by proton nuclear magnetic resonance (1H NMR) spectroscopy, and physical properties were compared with the literature values of known compounds. The spent polymeric reagent were regenerated quantitatively and reused for several cycles without significant loss of their activity.
- Karimi Zarchi, Mohammad Ali,Nazem, Fatemeh
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- HClO4-SiO2 as an efficient and reusable heterogeneous catalyst for the synthesis of 1-substituted tetrazoles
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An efficient and direct protocol is described for the preparation of 1-substituted 1H-1,2,3,4-tetrazoles by the reaction of primary amines, triethyl orthoformate and sodium azide in the presence of catalytic amount of silica-supported perchloric acid under solvent-free and heterogeneous conditions. The thermal solvent-free green procedure offers advantages such as simple methodology, easy work-up, high yield, recovery and reusability of catalyst.
- Bahari, Siavash,Rezaei, Akbar
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- Synthesis of 1-substituted tetrazoles using CoFe2O4 nanoparticles as a magnetically recoverable and reusable catalyst
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Nano CoFe2O4 is found to be efficient catalyst for synthesis of 1-substituted 1H-1,2,3,4-tetrazoles under solvent- free conditions. The significant advantages of this methodology are high yields, elimination of dangerous and harmful hydrazoic acid and simple work-up procedure. The catalyst was easily isolated from the reaction mixture by magnetic decantation using an external magnet and reused with no significant loss in its reactivity.
- Bahari, Siavash
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p. 527 - 531
(2013/08/23)
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- Highly efficient synthesis of 1- and 5-substituted 1H-tetrazoles using chitosan derived magnetic ionic liquid as a recyclable biopolymer-supported catalyst
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A general method for the efficient synthesis of 1- and 5-substituted 1H-tetrazoles from nitriles and amines is described using chitosan supported magnetic ionic liquid nanoparticles (CSMIL) as a novel heterogeneous catalyst. The application of this catalyst allows the synthesis of a variety of tetrazoles in high yields at low temperature. This new magnetic catalyst has been prepared from chitosan (the most abundant biopolymer in nature and cheap industrial waste) and methyl imidazole (a widely available backbone of ionic liquids) which was reacted with FeCl3 to obtain the CS-EMImFeCl4 catalyst. This methodology illustrates a very simple procedure, with wide applicability, environmental friendliness and reusability of catalyst. The new catalyst was characterized using some different microscopic and spectroscopic techniques such as transmission electron microscopy (TEM), scanning electron microscopy (SEM), FTIR spectroscopy, and Raman spectroscopy. The novel catalyst has therefore a great potential to be used in green processes. The Royal Society of Chemistry 2013.
- Khalafi-Nezhad, Ali,Mohammadi, Somayeh
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p. 4362 - 4371
(2013/05/08)
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- A stereocontrolled 1,2-addition reaction of tetrazoles with alkyl propiolates for the synthesis of highly functionalized enamines
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A stereocontrolled 1,2-addition reaction of 1-aryl-1H-tetrazoles with alkyl propiolates for the synthesis of highly functionalized enamines was developed. In the presence of silver oxide (Ag2O), the 1,2-addition reaction generated (Z)-N-cyano enamines in good yields with exclusive formation of the Z-isomers. Meanwhile, the 1,2-addition reaction generated (E)-N-cyano enamines in the presence of Ag2O and potassium carbonate (K2CO 3) with high stereoselectivity and yields. Copyright
- Luo, Kai,Meng, Lingguo,Zhang, Yicheng,Zhang, Xiuli,Wang, Lei
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p. 765 - 780
(2013/04/10)
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- HIV PROTEASE INHIBITORS
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Compounds of Formula I are disclosed: wherein A, R1, R2, R3, R4A, R4B, R5, R6 and R7 are defined herein. The compounds encompassed by Formula I include compounds which
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Page/Page column 33
(2013/05/21)
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- Building heterocyclic systems with RC(OR)2+ carbocations in recyclable bronsted acidic ionic liquids: Facile synthesis of 1-substituted 1H-1,2,3,4-tetrazoles, benzazoles and other ring systems with CH(OEt)3 and EtC(OEt)3 in [EtNH 3][NO3] and [PMIM(SO3H)][OTf]
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1-Aryl/alkyl-1H-1,2,3,4-tetrazoles can conveniently be synthesized in one-pot reactions from the corresponding amines by reaction with TMSN 3 and CH(OEt)3 using the readily available, recyclable, Bronsted acidic ionic liquids [EtNH3][NO3] IL-1 and [PMIM(SO3H)][OTf] IL-2 under mild conditions in high yields. Based on comparative reactions, whereas both ILs are excellent promoters, reactions are completed with shorter reaction times and in higher yields with IL-2. Among 24 examples provided, identical products were obtained via the two ILs, except in the case of 2-aminobenzoic acid where tetrazole was formed with IL-2 and 2-ethylquinazolin-4(3H)-one was formed with IL-1. By leaving out TMS-N 3 from the reaction, the in-situ formed CH(OEt)2 + and EtC(OEt)2+ (via their corresponding orthoesters) react under sonication with o-phenylenediamine bearing various substituents, o-aminothiophenol and o-aminophenol to form a wide array of benzazoles (benzimidazole, benzothiazole and benzoxazole) and quinazolin-4(3H)-one in high yields (18 examples). The two ILs reacted differently in reaction with 2-aminobenzamide, whereas quinazolin-4(3H)one was formed with IL-2/CH(OEt)3, the "unexpected" N-ethylquinazolin-4(3H)one was isolated with IL-1/CH(OEt)3. The latter was also formed from 2-aminobenzoic acid in IL-1/CH(OEt)3. Mechanistic implications are addressed. The reported protocols enable rapid assembly of a host of heterocyclic systems in high yields with the added advantage of recycling and re-use of the ILs.
- Aridoss, Gopalakrishnan,Laali, Kenneth K.
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experimental part
p. 2827 - 2835
(2011/06/23)
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- Green synthesis of the 1-substituted 1H-1,2,3,4-tetrazoles by application of the Natrolite zeolite as a new and reusable heterogeneous catalyst
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An efficient method for the preparation of 1-substituted 1H-1,2,3,4-tetrazoles is reported using Natrolite zeolite as a natural and heterogeneous catalyst under solvent-free conditions. This method has the advantages of high yields, simple methodology and easy work-up. The catalyst can be recovered by simple filtration and reused in good yields.
- Habibi, Davood,Nasrollahzadeh, Mahmoud,Kamali, Taghi A.
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supporting information; experimental part
p. 3499 - 3504
(2012/01/06)
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- Efficient uncatalyzed conversion of primary and secondary thioamides into 1-substituted, 5-substituted, 1, 5-disubstituted and annulated tetrazoles
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Unprecedented high-yield simple and mild conversion of primary aliphatic and aromatic thioamides into 5-substituted tetrazoles on treatment with a combination of tetrachlorosilane and sodium azide in refluxing acetonitrile has been achieved. Secondary acyclic, cyclic, and heterocyclic thioamides could also be transformed in high yields into 1-substituted, 1,5-disubstituted, or annulated tetrazoles under the same reaction condition. Copyright Taylor & Francis Group, LLC.
- El-Ahl, Abdel-Aziz S.,Amer, Fatty A.,Elbeheery, Akram H.
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experimental part
p. 2226 - 2235
(2012/03/26)
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- Synthesis and transformations of 1-(azidophenyl)-1H-tetrazoles
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Diazotization of 1-(aminophenyl)-1H-tetrazoles and subsequent treatment of the diazonium salts with sodium azide gave 1-(azidophenyl)-1H-tetrazoles which were brought into cyclization with ethyl acetoacetate and cyanoacetanilide to obtain 1,2,3-triazole derivatives. Under these conditions, the tetrazole ring may undergo cleavage with formation of cyanamide group.
- Pokhodylo,Matiichuk,Obushak
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experimental part
p. 556 - 560
(2010/08/20)
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- Synthesis of 2,1-benzisoxazoles by nucleophilic substitution of hydrogen in nitroarenes activated by the azole ring
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Reaction of 1-nitro-4-(1,2,3-triazolyl/tetrazolyl)benzenes with arylacetonitriles in an alcoholic medium in the presence of excess alkali gives novel 2,1-benzisoxazoles. These findings indicate a high reactivity of nitroarenes activated by the azole ring due to their electron-deficient character. Moreover, it was found that annulation of the isoxazole ring occurred regioselectively in disubstituted nitroarenes. In the case of 1-(4-nitrophenyl)-1H-tetrazole, the tetrazole ring cleaved faster than the sH-adduct was formed. Georg Thieme Verlag Stuttgart.
- Pokhodylo, Nazariy T.,Teslenko, Yuriy O.,Matiychuk, Vasyl S.,Obushak, Mykola D.
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scheme or table
p. 2741 - 2748
(2010/02/28)
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- NITROGEN CONTAINING HETEROAROMATICS AS FACTOR Xa INHIBITORS
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The present application describes nitrogen containing heteroaromatics and derivatives thereof of formula (I) or pharmaceutically acceptable salt or prodrug forms thereof, wherein J is N or NH and D may be C(=NH)NH2, which are useful as inhibitors of factor Xa.
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Page/Page column 68
(2009/10/01)
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- One-pot syntheses of 5-amino-1-aryltetrazole derivatives
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A novel facile route for the introduction of 5-amino and 5-alkylamino substituents into 1-aryltetrazoles has been developed. A range of 5-amino-1-aryltetrazoles was obtained directly from the corresponding 1-aryltetrazoles in one pot by consecutive ring-opening, azidation and intramolecular cyclization. 5-Alkylamino-1-aryltetrazoles were formed by a similar mechanism from 1,4-disubstituted tetrazolium salts. An influence of the nature of aryl substituents and reaction conditions on the regioselectivity of the intramolecular cyclization of intermediate guanyl azides is revealed. Georg Thieme Verlag Stuttgart.
- Vorobiov, Andrey N.,Gaponik, Pavel N.,Petrov, Petr T.,Ivashkevich, Oleg A.
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p. 1307 - 1312
(2007/10/03)
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- Optically active antifungal azoles. XI. An alternative synthetic route for 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-hydroxy-1-methyl-3-(1H-1,2,4-triazol-1-yl )propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone (TAK-456) and its analog
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New routes for the synthesis of the optically active antifungal triazoles 1-[(1R,2R)-2-(2,4-difluorophenyl)-2-Hydroxy-1-Methyl-3-(1H-1,2,4-triazol-1-Yl )propyl]-3-[4-(1H-1-tetrazolyl)phenyl]-2-imidazolidinone (1b) and the 3-[4-(1H-1,2,3-triazol-1-Yl)phenyl]-2-imidazolidinone analog (1a) that possess an imidazolidine nucleus were established. The key synthetic intermediates, (2R,3R)-3-(2,2-diethoxyethyl)amino-2-(2,4-difluorophenyl)-1-(1H-1,2,4-triazol -1-Yl)-2-butanol (8) and (2R,3R)-2-(2,4-difluorophenyl)-3-(2-hydroxyethyl)amino-1-(1H-1,2,4-triazol-1- yl)-2-butanol (14), were prepared by the ring-Opening reaction of the oxirane (2) with the corresponding 2-Substituted ethylamines. The acetal (8) was converted to the imidazolidinones (1a, b) by condensation with the carbamates (10a, b) followed by treatment with hydrochloric acid and subsequent catalytic hydrogenation. The candidate selected for the clinical trials, 1b (TAK-456), was alternatively prepared from the hydroxyethylamino intermediate (14) via two reaction steps: condensation with the carbamate (10b) to the urea (15) and subsequent cyclization to the imidazolidinones. This newly developed synthetic route could be applied to a large scale preparation of 1b.
- Ichikawa, Takashi,Kitazaki, Tomoyuki,Matsushita, Yoshihiro,Hosono, Hiroshi,Yamada, Masami,Mizuno, Masahiro,Itoh, Katsumi
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p. 1947 - 1953
(2007/10/03)
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- Nitrogen containing heteroaromatics as factor Xa inhibitors
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The present application describes nitrogen containing heteroaromatics and derivatives thereof of formula I: or pharmaceutically acceptable salt or prodrug forms thereof, wherein J is N or NH and D may be C(=NH)NH2, which are useful as inhibitors of factor Xa.
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- SYNTHESIS AND PROPERTIES OF PHENYLENEBIS-1H-TETRAZOLES
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Heterocyclization of m- and p-phenylenediamines with orthoformic ester and sodium azide has given phenylenebis-1H-tetrazoles.Under these conditions, o-phenylenediamine gives benzimidazole. o-, m-, and p-Phenylenebis-1H-tetrazoles were also obtained from the nitroanilines via the intermediate nitro- and aminophenyltetrazoles.The reactions of the bistetrazoles examined were basic hydrolysis, aminomethylation, and complex formation with copper salts.
- Gaponik, P. N.,Karavai, V. P.,Davshko, I. E.,Degtyarik, M. M.,Bogatikov, A. N.
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p. 1274 - 1278
(2007/10/02)
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- REACTIONS OF TRIMETHYLSILYL AZIDE WITH ALDEHYDES: FACILE AND CONVENIENT SYNTHESES OF DIAZIDES, TETRAZOLES, AND NITRILES
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The reactions of trimethylsilyl azide (TMSA) with various aldehydes were found to be versatile procedures for the synthesis of gem- and 1,3-diazides, tetrazoles, and nitriles, whose formation was varied by controlling the quantities of TMSA, catalyst, and the reaction conditions.
- Nishiyama, Kozaburo,Oba, Makoto,Watanabe, Akio
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p. 693 - 700
(2007/10/02)
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