- Aza-Riley Oxidation of Ugi-Azide and Ugi-3CR Products toward Vicinal Tricarbonyl Amides: Two-Step MCR-Oxidation Methodology Accessing Functionalized α,β-Diketoamides and α,β-Diketotetrazoles
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Direct oxidative deamination of glyoxal-derived Ugi-azide and Ugi three-component reaction products readily affords vicinal tricarbonyls (α,β-diketoamides) and α,β-diketotetrazoles with two diversity elements. This significant extension of our previously described multicomponent reaction-oxidative deamination methodology is proposed to proceed through a mechanistically distinct SeO2-mediated C-N oxidation derived from an active enol of α-amino-β-ketone systems, effectively an aza-Riley oxidation. This methodology accesses diverse VTC systems from prototypical amines, glyoxaldehydes, and isocyanide building blocks in a mere two steps.
- Foley, Christopher,Shaw, Arthur,Hulme, Christopher
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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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- 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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p. 19203 - 19220
(2021/06/03)
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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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- [3+1+1] type cyclization of ClCF2COONa for the assembly of imidazoles and tetrazolesvia in situgenerated isocyanides
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A facile synthesis of imidazoles and tetrazolesvia[3+1+1] type cyclization of ClCF2COONa is developed. A diverse array of imidazoles and tetrazoles were obtained in decent yieldsviaisocyanide intermediates. Notably, this is the first example of the cycloaddition ofin situgenerated isocyanides.
- Song, Qiuling,Wang, Ya,Zhou, Yao
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supporting information
p. 6106 - 6109
(2020/06/10)
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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 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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- 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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- Docking, Synthesis, Spectral Characterization, and Evaluation of In Vitro Antifungal Activity of Bis/Monophenyl-1-aryl-1H-tetrazole-5-carboxylate
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Some novel compounds of bis/monophenyl-1-aryl-1H-tetrazole-5-carboxylate were synthesized by the equimolar reaction between bis/mono-1-aryl-1H-tetrazole and phenyl chloroformate in the presence of NaOH in dry tetrahydrofuran. The content was stirred for 4
- Sambandam, Chandrakumari,Dhanavel, Sivakumar,Haridoss, Manikandan,Mannuthusamy, Gopalakrishnan
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p. 2779 - 2786
(2019/08/26)
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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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- 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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- 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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- Five-membered N-Heterocycles Synthesis Catalyzed by Nano-silica Supported Copper(II)–2-imino-1,2-diphenylethan-1-ol Complex
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Abstract: In this study, a new amino functionalized nano silica was synthesized using 2-hydroxy-1,2-diphenylethan-1-one. The new 2-hydroxy-1,2-diphenylethan-1-one@amino functionalized nano-silica was used as a support material for copper(II) catalyst. This composite was characterized by various techniques such as transmission electron microscopy, field emission scanning electron microscope, X-ray powder diffraction, inductively coupled plasma, energy dispersive X-ray spectroscopy, thermal gravimetric and FT-IR analysis and its particles size was estimated to be between 20 and 30?nm. The catalyst was tested in the N-heterocycles synthesis via C–N bond forming reactions. The catalyst displayed outstanding catalytic activity for all reactions under mild conditions. Finally, the nano heterogeneous copper catalyst is recoverable up to 12 times without any significant leaching which indicated that the heterogeneous catalyst is stable and very active under the applied conditions. Graphical Abstract: [Figure not available: see fulltext.]
- Sharghi, Hashem,Shiri, Pezhman,Aberi, Mahdi
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p. 2844 - 2862
(2017/09/25)
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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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- 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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p. 897 - 904
(2016/10/18)
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- Ultrasound-promoted one-pot three component synthesis of tetrazoles catalyzed by zinc sulfide nanoparticles as a recyclable heterogeneous catalyst
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Ultrasound irradiation was applied for the appropriate and rapid synthesis of 1-substituted tetrazoles through cyclization reaction of various primary amines, sodium azide and triethyl orthoformate. This reaction was effectively catalyzed by ZnS nanoparti
- Naeimi, Hossein,Kiani, Fatemeh
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p. 408 - 415
(2015/06/30)
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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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- Sulfonic acid-functionalized silica-coated magnetic nanoparticles as an efficient reusable catalyst for the synthesis of 1-substituted 1H-tetrazoles under solvent-free conditions
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Regarding green chemistry goals, silica-coated magnetite nanoparticles open up a new avenue to introduce a very useful and efficient system for facilitating catalyst recovery in different organic reactions. Therefore, in this paper the preparation of sulf
- Naeimi, Hossein,Mohamadabadi, Samaneh
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supporting information
p. 12967 - 12973
(2014/08/18)
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- Green synthesis of 5-substituted-1H-1,2,3,4-tetrazoles and 1-sustituted-1H-1,2,3,4-tetrazoles via [3+2] cycloaddition by reusable immobilized AlCl3on -Al2O3
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We report the effectiveness of the surface modified γ-Al2O3which is reusable, efficient, catalytic, safe and environmentally acceptable procedure for the conversion of both alkyl and aryl nitriles into the corresponding 5-substituted-1H-1,2,3,4-tetrazoles via [3+2] cycloaddition with sodium azide in excellent yields at mild reaction conditions (50 ° C). The catalyst also afforded 1-substituted-1H-1,2,3,4-tetrazoles by the reaction of amines, sodium azide and triethyl orthoformate. The catalyst could be recycled and was reused eleven runs without losing its activity.
- Nanjundaswamy, Hemmaragala Marishetty,Abrahamse, Heidi
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p. 2137 - 2150
(2015/01/09)
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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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- 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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- Solvent-free synthesis of 1-aryl-1H-1,2,3,4-tetrazoles using FeCl 3-SiO2 catalysis under conventional and ultrasound irradiation conditions
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1-Aryl-1H-1,2,3,4-tetrazoles were synthesised by the solvent-free reactions of aryl amines, sodium azide and triethyl orthoformate using FeCl 3-SiO2 as an effective heterogeneous catalyst under conventional and ultrasound irradiation
- Habibi, Davood,Mostafaee, Samaneh,Mehrabi, Leila
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p. 464 - 466
(2013/09/12)
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- Facile synthesis of 5-substituted-1H-tetrazoles and 1-substituted-1H- tetrazoles catalyzed by recyclable 4′-phenyl-2,2′:6′,2″- terpyridine copper(II) complex immobilized onto activated multi-walled carbon nanotubes
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5-Substituted-1H-tetrazoles can conveniently be synthesized from the corresponding nitriles by reaction with NaN3 using the efficient and recyclable heterogeneous catalyst prepared by immobilization of copper(II) complex of 4′-phenyl-2,2′:6′,2″-terpyridine on activated multi-walled carbon nanotubes [AMWCNTs-O-Cu(II)-PhTPY]. Excellent results were obtained in each case affording the corresponding tetrazole adducts in good to excellent yields. In general, aromatic nitriles with electron-donating group could be accomplished as well as that with electron-withdrawing groups. By leaving out nitrile from the reaction and adding CH(OEt)3 and amines bearing various substituents, 1-substituted-1H-tetrazoles formed in water in high yields. The reported protocols have the advantages of rapid assembly of a host of heterocyclic systems in high yields with the added advantage of recycling and reuse of the catalyst.
- Sharghi, Hashem,Ebrahimpourmoghaddam, Sakineh,Doroodmand, Mohammad Mahdi
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- P2O5-SiO2 as an efficient heterogeneous catalyst for the solvent-free synthesis of 1-substituted 1H-1,2,3,4-tetrazoles under conventional and ultrasound irradiation conditions
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1-Substituted 1H-1,2,3,4-tetrazoles were efficiently synthesized from the reaction of primary amines, triethyl orthoformate, and sodium azide in presence of a catalytic amount of P2O5-SiO2 under conventional and ultrasound irradiation in solvent-free conditions. The advantages of this procedure are high yields, relatively short reaction times, ease of product isolation, low cost, and recovery and reusability of the catalyst.
- Habibi, Davood,Nasrollahzadeh, Mahmoud,Mehrabi, Leila,Mostafaee, Samaneh
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p. 725 - 728
(2013/07/26)
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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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- 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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- 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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- BICYCLIC HETEROARYL COMPOUNDS AS GPR119 RECEPTOR AGONISTS
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The present invention provides a new class of bicyclic heteroaryl compounds represented by Formula (I), pharmaceutical compositions containing these compounds, and their use for modulating the activity of GPR119 in the treatment of metabolic disorders and complications thereof, as well as methods for the treatment of the metabolic disorders and complications thereof.
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Page/Page column 32
(2012/08/27)
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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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