- Assembly of super-supertetrahedral metal-organic clusters into a hierarchical porous cubic framework
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A porous framework comprising a super-supertetrahedral metal-organic cluster building block has been synthesized. Its cubic framework represents a multi-level hierarchical architecture and also possesses an interesting magnetic property.
- Wang, Le,Morales, Jason,Wu, Tao,Zhao, Xiang,Beyermann, Ward P.,Bu, Xianhui,Feng, Pingyun
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- PROCESS FOR PREPARING 5-SUBSTITUTED-1H-TETRAZOLES IN AQUEOUS BETAINE SOLUTION
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The present invention relates to a method for manufacturing 5-substituted-1H-tetrazole in an aqueous betaine solution. More specifically, the present invention relates to a method for manufacturing 5-substituted-1H-tetrazole which comprises: a step of con
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Paragraph 0103-0108
(2020/06/13)
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- Allylic oxidation of olefins with a manganese-based metal-organic framework
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Selective oxidation of olefins to α,β-unsaturated ketones under mild reaction conditions has attracted considerable interest, since α,β-unsaturated ketones can serve as synthetic precursors for various downstream chemical products. The major inherent challenges with this chemical oxidation are chemo- and regio-selectivity as well as environmental concerns, i.e. catalyst recycle, safety and cost. Using atmospheric oxygen as an environmentally friendly oxidant, we found that a metal-organic framework (MOF) constructed with Mn and a tetrazolate ligand (CPF-5) showed good activity and selectivity for the allylic oxidation of olefins to α,β-unsaturated ketones. Under the optimized conditions, we could achieve 98% conversion of cyclohexene and 87% selectivity toward cyclohexanone. The combination of a substoichiometric amount of TBHP (tert-butylhydroperoxide) and oxygen not only provides a cost effective oxidation system but significantly enhances the selectivity to α,β-unsaturated ketones, outperforming most reported oxidation methods. This catalytic system is heterogeneous in nature, and CPF-5 could be reused at least five times without a significant decrease in its catalytic activity and selectivity.
- Chen, Jingwen,Chen, Minda,Zhang, Biying,Nie, Renfeng,Huang, Ao,Goh, Tian Wei,Volkov, Alexander,Zhang, Zhiguo,Ren, Qilong,Huang, Wenyu
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supporting information
p. 3629 - 3636
(2019/07/10)
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- Tin-Catalyzed Synthesis of 5-Substituted 1H-Tetrazoles from Nitriles: Homogeneous and Heterogeneous Procedures
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The preparation of 5-substituted 1H-tetrazoles was efficiently achieved by reaction of trimethylsilylazide with nitriles using a triorganotin alkoxide precatalyst. The reaction mechanism was first investigated using a homogeneous tributyltin derivative and was explored through experimental investigations and DFT calculations. A heterogeneous version was then developed using a polymer-supported organotin alkoxide and afforded an efficient method for the preparation of tetrazoles in high yields with an easy work-up and a residual tin concentration in the desired products compatible for pharmaceutical applications (less than 10 ppm). (Figure presented.).
- Chrétien, Jean-Mathieu,Kerric, Gaelle,Zammattio, Fran?oise,Galland, Nicolas,Paris, Michael,Quintard, Jean-Paul,Le Grognec, Erwan
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supporting information
p. 747 - 757
(2019/01/04)
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- A zinc(ii) metal-organic framework with high affinity for CO2 based on triazole and tetrazolyl benzene carboxylic acid
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A new metal-organic framework {[Zn2(Htzba)2(dmtrz)]·(CH3)2NH}n (1) that has already been solvothermally synthesized exhibits a high CO2 uptake capacity based on experimental and simulation calculation results. Furthermore, the selectivities to CO2/CH4 and CO2/N2 are predicted by IAST to be 41.19 and 46.21 at 298 K and 100 kPa, respectively. The superior performance suggests that 1 is a promising candidate for CO2 separation.
- Sheng, Donghai,Zhang, Ying,Han, Yang,Xu, Guang,Song, Qingxiang,Hu, Yanping,Liu, Xiangyun,Shan, Dongming,Cheng, Achao
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p. 3679 - 3685
(2019/06/24)
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- A Metal–Organic Framework with Exceptional Activity for C?H Bond Amination
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The development of catalysts capable of fast, robust C?H bond amination under mild conditions is an unrealized goal despite substantial progress in the field of C?H activation in recent years. A Mn-based metal–organic framework (CPF-5) is described that promotes the direct amination of C?H bonds with exceptional activity. CPF-5 is capable of functionalizing C?H bonds in an intermolecular fashion with unrivaled catalytic stability producing >105 turnovers.
- Wang, Le,Agnew, Douglas W.,Yu, Xiao,Figueroa, Joshua S.,Cohen, Seth M.
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supporting information
p. 511 - 515
(2018/02/21)
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- KIT-6-anchored sulfonic acid groups as a heterogeneous solid acid catalyst for the synthesis of aryl tetrazoles
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In the current study, a simple, environmentally benign and cost-effective method is presented for the preparation of 5-substituted-1H-aryltetrazoles. To this goal, mesoporous KIT-6 silica anchored with sulfonic acid (–SO3H) groups via post-grafting modification was synthesized using the sol–gel method and characterized by XRD, TGA, FTIR, BET, TEM and SEM techniques. For the preparation of tetrazole derivatives, the effect of various parameters such as catalyst amount, aryl nitrile:azide ratio, temperature and reaction time was tested. The hybrid organic/inorganic catalyst could be recovered easily through a simple filtration and reused multiple times without significant loss in activity.
- Najafi Chermahini, Alireza,Andisheh, Nikzad,Teimouri, Abbas
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p. 831 - 838
(2018/03/01)
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- Tetrazoles: Calcium oxalate crystal growth modifiers
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Molecules containing tetrazole substituents have become of interest due to their being bioisosteres of carboxylic acids and like their carboxylate counterparts, tetrazolate anions have been able to affect the crystal growth of barium sulphate and calcium carbonate. In this proof of principle study, we show that this behaviour also extends to calcium oxalate and therefore opens the possibility of using tetrazole-based additives for investigating mineralization processes of human pathological relevance. This journal is
- McMulkin, Calum J.,Massi, Massimiliano,Jones, Franca
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p. 2675 - 2681
(2015/03/30)
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- Microwave Synthesis of 5-Substituted 1 H-Tetrazoles Catalyzed by Bismuth Chloride in Water
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(Chemical Equation Presented). Bismuth chloride was used to catalyze the [2 + 3] cycloaddition between sodium azide with aryl nitriles, aliphatic nitriles, and vinyl nitriles. A number of 5-substituted 1H-tetrazoles were synthesized in water or isopropano
- Coca, Adiel,Feinn, Liana,Dudley, Joshua
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p. 1023 - 1030
(2015/03/30)
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- Application of a functionalized mesoporous silica catalyst to the synthesis of tetrazoles
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In the present study, well ordered MCM-41 was synthesized and functionalized with benzyl group and subsequently sulfonated with chlorosulfonic acid. The functionalized catalyst (MCMBSA) was characterized by XRD, TGA, FTIR, TEM, BET, and SEM. 5-Aryl-1H-tetrazoles were synthesized by the reaction of the corresponding aryl nitriles and sodium azide catalyzed by MCMBSA. The mole ratio of nitrile to sodium azide, the amount of catalyst, reaction times, and solvent type were optimized. The MCMBSA catalyst was more effective than the catalyst obtained from the direct sulfonation of MCM-41. The versatility of the method was investigated by using various nitriles, which showed reasonable yields of tetrazoles. The regeneration and reusability of catalyst was also examined.
- Najafi Chermahini, Alireza,Khani Omran, Masoud,Dabbagh, Hossein A.,Mohammadnezhad, Gholamhossein,Teimouri, Abbas
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p. 4814 - 4820
(2015/06/16)
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- The synthesis of tetrazoles in nanometer aqueous micelles at room temperature
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A newly developed nonionic amphiphile (GPGS-1500), a diester composed of a Guerbet alcohol (2-octyldodecan-1-ol), poly(ethylene glycol) 1500 (PEG 1500), and succinic acid esters, has been prepared as an effective nanomicelle-forming species for the synthesis of tetrazoles in water at room temperature. We have designed a new nonionic amphiphile (GPGS-1500) for the synthesis of tetrazoles in water at room temperature. The reaction conditions were optimized, and the size of the micelles formed by GPGS-1500 in water was measured by dynamic light scattering. Copyright
- Xie, Aming,Cao, Meiping,Liu, Yangyang,Feng, Liandong,Hu, Xinyu,Dong, Wei
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p. 436 - 441
(2014/01/23)
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- The Synthesis of Tetrazoles in Nanometer Aqueous Micelles at Room Temperature
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A newly developed nonionic amphiphile (GPGS-1500), a diester composed of a Guerbet alcohol (2-octyldodecan-1-ol), poly(ethylene glycol) 1500 (PEG 1500), and succinic acid esters, has been prepared as an effective nanomicelle-forming species for the synthesis of tetrazoles in water at room temperature.
- Xie, Aming,Cao, Meiping,Liu, Yangyang,Feng, Liandong,Hu, Xinyu,Dong, Wei
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p. 436 - 441
(2015/10/05)
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- The synthesis of 5-substituted 1H-tetrazoles in molten tetrabutylammonium bromide
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An economical and environmentally benign method for the synthesis of 5-substituted 1H-tetrazoles has been established. In this protocol, molten tetrabutylammonium bromide (TBAB) is used as both the solvent and catalyst. A mechanism involving the intermedi
- Xie, Aming,Cao, Meiping,Feng, Liandong,Dong, Wei
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p. 665 - 667
(2014/01/17)
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- Going from green to red electroluminescence through ancillary ligand substitution in ruthenium(ii) tetrazole benzoic acid emitters
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The synthesis, characterization, photoluminescence (PL) and electroluminescence (EL) properties of novel ruthenium(ii) emitters with 4-(1H-tetrazole-5-yl)benzoic acid (TzBA) as a novel basic ligand and 2,2-bipyridine (bpy), 1,10-phenanthroline (phen) and pyridine tetrazole (pyTz) as ancillary ligands have been reported. The EL results show that the luminescence of Ru(TzBA) depends on the ancillary ligands, which can be used to tune the EL color of the Ru(TzBA) complexes from green to red emission. The role of ancillary ligands in EL devices of the Ru(TzBA) complexes was investigated by DFT calculations. The device [Ru(TzBA)(bpy)(pyTz)(SCN)] (5) has a luminance of 480 cd m-2 and a maximum efficiency of 1.2 cd A-1 at 16 V, which are the highest values among the five devices studied. The turn-on voltage of this device is approximately 6 V. We suggest that an electroplex occured at the PVK-Ru complex interface when pyTz was incorporated as an ancillary ligand into Ru(TzBA). OLED studies reveal that pyTz as an ancillary ligand exhibits better current generating capacity than bpy and phen ligands, which are introduced by an emitter (5).
- Shahroosvand, Hashem,Najafi, Leyla,Sousaraei, Ahmad,Mohajerani, Ezeddin,Janghouri, Mohammad
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p. 6970 - 6980
(2013/10/22)
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- Zeolite and sulfated zirconia as catalysts for the synthesis of 5-substituted 1H-tetrazoles via [2+3] cycloaddition of nitriles and sodium azide
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The [2+3] cycloaddition between various nitriles and sodium azide proceeds smoothly in the presence of zeolite and sulfated zirconia as effective catalysts, in water and DMF/MeOH, to give the corresponding 5-substituted 1H-tetrazoles in good to high yields. The reaction most probably proceeds through the in situ formation of catalyst azide species, followed by a successive [2+3] cycloaddition with the nitriles. This method has the advantages of high yields, simple methodology and easy work-up. The catalyst can be recovered by simple filtration and reused with good yields.
- Teimouri, Abbas,Najafi Chermahini, Alireza
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experimental part
p. 2606 - 2610
(2011/10/09)
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- Clay-catalyzed synthesis of 5-substituent 1-H-tetrazoles
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In this study, the possibility of 5-substituted 1-H-tetrazoles synthesis using clays as catalyst was investigated. The reaction of a series of aromatic nitriles with sodium azide was catalyzed by montmorillonite K-10 or kaolin clays in water or DMF as solvent. Conventional heating or ultrasonic irradiation was used to promote reaction. The amount of nitrile to sodium azide mole ratio, amount of catalyst, reaction time, and solvent type were optimized. The versatility of this method was checked by using various nitriles, which showed reasonable yields of tetrazole formation. It was found that using nitriles with electron-with-drawing groups result in both higher yields and lower reaction times. The catalysts could be reused several times without significant loss of their catalytic activity. Compared to conventional heating, ultrasonic irradiation reduced reaction times and increased catalyst activity. The present procedure is green and offers advantages, such as shorter reaction time, simple workup, and recovery and reusability of catalyst.
- Chermahini, Alireza Najafi,Teimouri, Abbas,Momenbeik, Fariborz,Zarei, Amin,Dalirnasab, Zeinab,Ghaedi, Aseyeh,Roosta, Mostafa
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experimental part
p. 913 - 922
(2010/09/03)
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- PHARMACEUTICAL PREPARATIONS COMPRISING INSULIN, ZINC IONS AND A ZINC-BINDING LIGAND
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Novel preparations comprising branched ligands for the HisB10 Zn2+ sites of the R-state insulin hexamer. The preparations have a prolonged action designed for flexible injection regimes.
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Page/Page column 270
(2008/06/13)
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- MODULATORS OF ALPHA7 NICOTINIC ACETYLCHOLINE RECEPTORS AND THERAPEUTIC USES THEREOF
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The present invention relates to compounds with α7 nAChR agonistic activity, processes for their preparation, pharmaceutical compositions containing the same and the use thereof for the treatment of neurological, psychiatric, cognitive, immunological and inflammatory disorders.
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Page/Page column 24-25
(2010/02/15)
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- 5-Aryltetrazole Compounds, compositions thereof, and uses therefor
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The present invention relates to 5-Aryltetrazole compounds, compositions comprising a 5-Aryltetrazole compound, and methods for treating an inflammation disease, a reperfusion disease, hyperuricemia, gout, or tumor-lysis syndrome in an animal in need ther
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- SPECTRA AND ELECTRONIC STRUCTURE IN THE EXCITED STATE OF CARBOXY-5-PHENYLTETRAZOLES
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Absorption and luminescence spectra of ortho-, meta- and para-carboxy-5-phenyltetrazole in aqueous solutions at room and low temperature were measured.Investigations were carried out in super acidic to super basic media.Three dissociation forms were identified (anion, molecule and cation) and corresponding acid-base equilibrium constants in the ground state were determined spectrophotometrically, and in the first excited singlet state from titration curves.The latter ones for anion-molecule equilibrium are in agreement with those calculated by the Foerster cycle.The formation of a twisted internal charge transfer (TICT) excited state of the anion is discussed.
- Janic, I.,Kakas, M.
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p. 189 - 192
(2007/10/02)
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