Hierarchically porous AlPO-5-based microspheres as heterogeneous catalysts for the synthesis of 5-substituted 1H-tetrazoles via [3+2] cycloaddition

Kong, Dan; Liu, Yanyan; Zhang, Juan; Li, Hongbian; Wang, Xiangyu; Liu, Guangyu; Li, Baojun; Xu, Zheng

doi:10.1039/c4nj00034j

Cited by 35 publications

(24 citation statements)

References 43 publications

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“…Various methods have been reported for the synthesis of 5‐substituted 1 H ‐tetrazoles, which most of them are based on the addition of trimethylsilyl azide or sodium azide to nitrile group. The reactions were carried out by using catalysts such as nano‐CuFe 2 O 4 , COY zeolites, AlPO‐5 microporous molecular sieves, Fe 3 O 4 @SiO 2 /Salen of Cu(II), Zn/Al hydrotalcite, γ‐Fe 2 O 3 , Zn(OTf) 2 , AlCl 3 and Brønsted acid catalyst . Heravi and co‐workers have reported a method for the synthesis of 5‐substituted 1 H ‐tetrazoles by reaction of aldehydes, hydroxylamine and [bmim]N 3 in DMF at 120 °C .…”

Section: Introductionmentioning

confidence: 99%

Dendrimer‐encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe₃O₄@SiO₂ nanoparticles as a novel recyclable catalyst for N‐arylation of nitrogen heterocycles and green synthesis of 5‐substituted 1H‐tetrazoles

Esmaeilpour

Sardarian

Firouzabadi

2018

Applied Organom Chemis

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In this study, dendrimer-encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe 3 O 4 @SiO 2 nanoparticles were prepared via a multistepsynthesis. Then, the synthesized composite was fully characterized by various techniques such as fourier transform infrared (FT-IR) spectroscopy, X-ray diffraction (XRD), dynamic light scattering (DLS), UV-vis spectroscopy, energy dispersive X-ray analysis (EDX), thermogravimetric analysis (TGA) and vibration sample magnetometer (VSM). From the information gained by FE-SEM and TEM studies it can be inferred that the particles are mostly spherical in shape and have an average size of 50 nm. Also, the amount of Cu is determined to be 0.51 mmol/g in the catalyst by inductively coupled plasma (ICP) analyzer. This magnetic nano-compound has been successfully applied as a highly efficient, magnetically recoverable and stable catalyst for N-arylation of nitrogen heterocycles with aryl halides (I, Br) and arylboronic acids without using external ligands or additives. The catalyst was also employed in a one-pot, three-component reaction for the efficient and green synthesis of 5-substituted 1H-tetrazoles using various aldehydes, hydroxylamine hydrochloride and sodium azide in water. The magnetic catalyst can be easily separated by an external magnet bar and is recycled seven times without significant loss of its activity.

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Section: Introductionmentioning

confidence: 99%

Dendrimer‐encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe₃O₄@SiO₂ nanoparticles as a novel recyclable catalyst for N‐arylation of nitrogen heterocycles and green synthesis of 5‐substituted 1H‐tetrazoles

Esmaeilpour

Sardarian

Firouzabadi

2018

Applied Organom Chemis

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“…This is unlike traditional HEDMs such as 2,4,6‐trinitrotoluene (TNT), 1,3,5‐trinitro‐1,3,5‐triazinane (RDX), and 1,3,5,7‐tetranitro‐1,3,5,7‐tetrazocane (HMX) where the energies are derived from the oxidation of the carbon backbone . Triazole‐ and tetrazole‐based energetic materials possess unique characteristics in that they combine a nitrogen‐rich moiety with a substituent that can be tuned toward desirable properties of high densities, good thermal stabilities, and low sensitivities …”

Section: Introductionmentioning

confidence: 99%

Heats of formation and thermal stability of substituted 1,1′‐Azobis(tetrazole) compounds with an extended nitrogen chain

Pimienta

Patkowski

2018

Int J of Quantum Chemistry

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The molecular structures of 1,1′‐Azobis(tetrazole) (N10) and monosubstituted compounds involving F, CH3, CN, NH2, OH, OCH3, N3, NF2, NO2, and CH2NO2 groups are investigated using density functional theory. The heats of formation of these compounds are investigated using ab initio composite methods. Intrinsic reaction coordinate calculations are performed to determine the energies along the decomposition pathways. The optimized geometries of the N10 compounds indicate planar configurations consisting of aromatic nitrogen–nitrogen and carbon–nitrogen bonds. The stability and energy content of the substituted compounds are highly correlated with the nature of the substituents. Electron‐donating groups reduce the heats of formation but increase the exothermicity of the decomposition. The decomposition of the N10 compounds is classified into two general pathways: (1) a scheme involving straight‐up decomposition and (2) a scheme involving functional rearrangement. Compounds undergoing decomposition pathway (1) are more exothermic with lower rate‐determining activation barriers than those undergoing the latter pathway (2).

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“…[18][19][20]. The isomorphic replacement of the tetrahedral framework atoms by transition metal ions in the AlPO-5 structure have been widely investigated in order to change the acid and redox proprieties of this zeolite and thus expand its application [21][22][23][24][25][26][27][28]. NiAlPO-5 was used in electroanalytical applications only once before the present work, so this is the first time this sensor is applied to determine a metal ion in ethanolic media.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Sensor Based on NiAlPO‐5 for Determination of Cu²⁺ in Ethanol Biofuel

et al. 2017

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This work describes the development of electrochemical sensors based on graphite–polyurethane composite (GPU) modified with aluminophosphate zeolite type 5 (AlPO‐5) and nickel (II) incorporated aluminophosphate type 5 (NiAlPO‐5), in order to evaluate their performance for determination of Cu2+ in ethanol biofuel. These electrodes were initially characterized by cyclic voltammetry. The obtained results revealed that the NiAlPO‐5 with Ni/Al ratio 0.5 presented the best response in terms of sensitivity, and peak width at half height of Cu2+ voltamogramm, which indicate that on these conditions the NiAlPO‐5 electrode is viable for determination of this ion in biofuel samples by square wave stripping voltammetry. The obtained results revealed that the presence of Ni in the zeolite structure (NiAlPO‐5) improves the electrical properties, and increases the peak current for Cu2+ in comparison with the electrode based in AlPO‐5. The proposed method presented a linear response for Cu2+ with good results for limit of detection (9.4×10−9 mol L−1), accuracy (recovery of 115 %) and precision (RSD of 5.9 %).

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Hierarchically porous AlPO-5-based microspheres as heterogeneous catalysts for the synthesis of 5-substituted 1H-tetrazoles via [3+2] cycloaddition

Abstract: W-containing AlPO-5 microspheres were effective catalyst for the synthesis of 5-substituted 1H-tetrazoles by [3+2] cycloaddition.

Cited by 35 publications

References 43 publications

Dendrimer‐encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe₃O₄@SiO₂ nanoparticles as a novel recyclable catalyst for N‐arylation of nitrogen heterocycles and green synthesis of 5‐substituted 1H‐tetrazoles

Dendrimer‐encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe₃O₄@SiO₂ nanoparticles as a novel recyclable catalyst for N‐arylation of nitrogen heterocycles and green synthesis of 5‐substituted 1H‐tetrazoles

Heats of formation and thermal stability of substituted 1,1′‐Azobis(tetrazole) compounds with an extended nitrogen chain

Electrochemical Sensor Based on NiAlPO‐5 for Determination of Cu²⁺ in Ethanol Biofuel

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Hierarchically porous AlPO-5-based microspheres as heterogeneous catalysts for the synthesis of 5-substituted 1H-tetrazoles via [3+2] cycloaddition

Abstract: W-containing AlPO-5 microspheres were effective catalyst for the synthesis of 5-substituted 1H-tetrazoles by [3+2] cycloaddition.

Cited by 35 publications

References 43 publications

Dendrimer‐encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe3O4@SiO2 nanoparticles as a novel recyclable catalyst for N‐arylation of nitrogen heterocycles and green synthesis of 5‐substituted 1H‐tetrazoles

Dendrimer‐encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe3O4@SiO2 nanoparticles as a novel recyclable catalyst for N‐arylation of nitrogen heterocycles and green synthesis of 5‐substituted 1H‐tetrazoles

Heats of formation and thermal stability of substituted 1,1′‐Azobis(tetrazole) compounds with an extended nitrogen chain

Electrochemical Sensor Based on NiAlPO‐5 for Determination of Cu2+ in Ethanol Biofuel

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Dendrimer‐encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe₃O₄@SiO₂ nanoparticles as a novel recyclable catalyst for N‐arylation of nitrogen heterocycles and green synthesis of 5‐substituted 1H‐tetrazoles

Dendrimer‐encapsulated Cu(Π) nanoparticles immobilized on superparamagnetic Fe₃O₄@SiO₂ nanoparticles as a novel recyclable catalyst for N‐arylation of nitrogen heterocycles and green synthesis of 5‐substituted 1H‐tetrazoles

Electrochemical Sensor Based on NiAlPO‐5 for Determination of Cu²⁺ in Ethanol Biofuel