Use of tetrazoles in catalysis and energetic applications: Recent developments

Nasrollahzadeh, Mahmoud; Nezafat, Zahra; Bidgoli, Nayyereh Sadat Soheili; Shafiei, Nasrin

doi:10.1016/j.mcat.2021.111788

Cited by 44 publications

(26 citation statements)

References 326 publications

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“…[3,[11][12][13][14] Over the last decade, numerous homogeneous and heterogeneous materials including transition metal-containing catalysts for direct synthesis of pyranopyrazoles and 5-substituted 1H-tetrazoles have been developed using several organic and inorganic catalytic complexes such as palladium, copper, and nickel. [15][16][17][18][19][20][21][22][23] However, most of these methods outlined above suffer from disadvantages due to harsh operational conditions, limited substrate scope, using expensive and noble metal, toxic reagents, low efficiency, and environmental impacts. [14,24,25] Particularly, for the industrial implication of one-pot synthesis of pyranopyrazoles and 5-substituted 1H-tetrazoles, homogeneous catalysts are mainly restricted by difficulties of catalyst separation from the reaction media and recovery of the catalyst.…”

Section: Introductionmentioning

confidence: 99%

A novel cubic Zn‐citric acid‐based MOF as a highly efficient and reusable catalyst for the synthesis of pyranopyrazoles and 5‐substituted 1H‐tetrazoles

Koolivand

Nikoorazm

Ghorbani‐Choghamarani

et al. 2022

Applied Organom Chemis

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A highly stable and efficient heterogeneous catalyst was successfully prepared by hydrothermal reaction of Zinc nitrate with citric acid. To produce a novel Zn-based MOF catalyst, Zn ions were coordinated with the ligand functional groups that can be regarded as an alpha-hydroxy acid containing three carboxylic acids (COOH) and one hydroxyl (OH) group attached to the three-carbon skeleton. It was found that the Zn-CA-MOFs compound can participate as a catalyst in the synthesis of 5-substituted 1H-tetrazole and pyranopyrazole molecules, selectively and efficiently with high yield in a short period of time.As presented, the catalyst demonstrates excellent reusability and stability and can be recycled up to five times without significant loss of reactivity. Heterogeneity analysis showed that no leaching of active Zn species occurred during the recycling process of the heterogeneous Zn-CA-MOFs.

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Section: Introductionmentioning

confidence: 99%

A novel cubic Zn‐citric acid‐based MOF as a highly efficient and reusable catalyst for the synthesis of pyranopyrazoles and 5‐substituted 1H‐tetrazoles

Koolivand

Nikoorazm

Ghorbani‐Choghamarani

et al. 2022

Applied Organom Chemis

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“…Furthermore, this pharmacophore is widely used in drug design studies as an appropriate isostere of carboxylic acid functional group 92 – 99 . In addition, application of tetrazole derivatives as important widespread compounds in synthetic organic chemistry 100 , 101 , catalysis and energetic applications 102 , materials chemistry 103 , and as ligands in coordination chemistry 104 have led to the development of various efficient synthetic methods. Tetrazole derivatives are most commonly synthesized by [3 + 2] cycloaddition reaction of the corresponding azide and nitrile moieties 105 – 112 .…”

Section: Introductionmentioning

confidence: 99%

Design and characterization of an urea-bridged PMO supporting Cu(II) nanoparticles as highly efficient heterogeneous catalyst for synthesis of tetrazole derivatives

Valiey

Dekamin

2022

Sci Rep

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In this work, a new periodic mesoporous organosilica with urea-bridges produced by the reaction of (3-aminopropyl)triethoxysilane and toluene-2,4-diisocyanate (APS-TDU-PMO) is introduced. The obtained APS-TDU-PMO was found to be an appropriate support for loading of Cu(II) nanoparticles to afford supramolecular Cu@APS-TDU-PMO nanocomposite. Uniformity and mesoporosity of both synthesized nanomaterials including APS-TDU-PMO and Cu@APS-TDU-PMO were proved by different spectroscopic, microscopic or analytical techniques including FTIR, EDX, XRD, FESEM, TEM, BET, TGA and DTA. Furthermore, the prepared Cu@APS-TDU-PMO nanomaterial was also used, as a heterogeneous and recyclable catalyst, for the synthesis of tetrazole derivatives through cascade condensation, concerted cycloaddition and tautomerization reactions. Indeed, the main advantages of this Cu@APS-TDU-PMO is its simple preparation and high catalytic activity as well as proper surface area which enable it to work under solvent-free conditions. Also, the introduced Cu@APS-TDU-PMO heterogeneous catalyst showed good stability and reusability for six consecutive runs to address more green chemistry principles.

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“…Triazole is diffusely used to prepare flame retardants on account of its high nitrogen content and stable heterocyclic structure. [33][34][35] Cheng et al [36] synthesized a P/N-containing flame retardant (PPT) constructed with phosphaphenanthrene, phosphonate, and triazole. It was found that the LOI value of the modified epoxy thermoset with 10.4 wt% PPT (P content: 0.71wt%) was 31.2%, and passed the V-0 rating in the UL-94 test.…”

Section: Introductionmentioning

confidence: 99%

Thermal Stability and Flame Retardancy of Epoxy Resin with DOPO‐Based Compound Containing Triazole and Hydroxyl Groups

Zhao

Wang

Zhuang

et al. 2022

Macro Materials & Eng

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A reactive flame retardant (DTP) is successfully synthesized and characterized, and then incorporated into epoxy resin (EP) as a co‐curing agent. The thermal stabilities and flame‐retardant properties of epoxy thermosets are evaluated. Compared to neat EP, the thermogravimetric analysis (TG) results show that the thermal decomposition rate of EP/DTP is reduced by 45% and the char yield at 750 °C is increased by 67%, when the addition amount of DTP is 12 wt%. In the cone calorimetry test (CCT), the values of the peak of heat release rate (pk‐HRR), total heat release (THR), total smoke produce (TSP), and average of effective heat combustion (av‐EHC) of EP‐DTP‐12 are exhibited a reduction of 36.6%, 26.4%, 40.5%, and 23.6% relative to neat EP, respectively. Meanwhile, the value of the limiting oxygen index (LOI) of EP/DTP‐12 can reach 34.83%, and 6 wt% or more loading of DTP make EP/DTP pass the V‐0 rating in the UL‐94 test. Moreover, the flame‐retardant mechanism is investigated by thermogravimetric analysis/infrared spectrometry (TG‐IR) and scanning electron microscopy (SEM), which can be summarized into two aspects: the quenching effect of phosphorus‐containing radicals and diluting effect of nonflammable gases in the gas phase, and the barrier effect of char layer in the condensed phase.

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Use of tetrazoles in catalysis and energetic applications: Recent developments

Cited by 44 publications

References 326 publications

A novel cubic Zn‐citric acid‐based MOF as a highly efficient and reusable catalyst for the synthesis of pyranopyrazoles and 5‐substituted 1H‐tetrazoles

A novel cubic Zn‐citric acid‐based MOF as a highly efficient and reusable catalyst for the synthesis of pyranopyrazoles and 5‐substituted 1H‐tetrazoles

Design and characterization of an urea-bridged PMO supporting Cu(II) nanoparticles as highly efficient heterogeneous catalyst for synthesis of tetrazole derivatives

Thermal Stability and Flame Retardancy of Epoxy Resin with DOPO‐Based Compound Containing Triazole and Hydroxyl Groups

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