- Rapidly, highly yielded and green synthesis of dihydrotetrazolo[1,5-a]pyrimidine derivatives in aqueous media using recoverable Pd (II) thiazole catalyst accelerated by ultrasonic: Computational studies
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Here, we synthesized new thiazole complexes from Cu (II), Fe (III), and Pd (II) ions. Such complexes were characterized to present their chemical formulae, firstly. The octahedral geometry was suggested for the investigated complexes except Pd (II) complex (ARPTPd), which has a square-planer arrangement. ARPTPd was planned to be used as a catalyst for synthesis of dihydrotetrazolo[1,5-a]pyrimidine derivatives at mild conditions. The catalytic activity of ARPTPd complex in four-components reaction approach was deliberately monitored till it reaches the most favorable conditions. The advantages of suggested catalyst were basically summarized by using green solvent (H2O), lower reaction time, and high products yields. Also, the superiority of ARPTPd complex and ultrasonic irradiation towards synthesis of dihydrotetrazolo[1,5-a]pyrimidine derivatives was revealed compared with other Lewis acids, basic, and ionic liquid catalysts. Furthermore, the mildness of conversion and compatibility with different functional groups makes it attractive. In addition, in consecration, computational aspects were often taken according to their effect on the declaration or discrimination of variable functional characteristics. Crystal packing systems of complexes were configured to extract important surface properties. DFT study was also applied to explain the causes behind the superiorly of ARPTPd complex. Also, the optimization process for intermediates was executed to support the suggested mechanism. Finally, this simple, economical, and green catalytic procedure may be applied to the industry in future.
- Abu-Dief, Ahmed M.,Alsoliemy, Amerah,El-Dabea, Tarek,El-Metwaly, Nashwa M.,El-Remaily, Mahmoud Abd El Aleem Ali Ali,Khalifa, Mohamed E.,Soliman, Ahmed M. M.
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- Preparation method of 1-tetrazole acetate
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The invention relates to the field of organic synthesis, and discloses a preparation method of 1-tetrazole acetate, which comprises the following steps: 1) taking aminoguanidine carbonate as a raw material, regulating to acidity with an acid solution, cooling, dropwisely adding a sodium nitrite water solution, regulating the pH value to alkalinity, and carrying out reflux cyclization to generate 5-aminotetrazole; 2) reacting 5-aminotetrazole with chloroacetic acid under an alkaline condition to synthesize 1-acetic acid-5-aminotetrazole, and 3) finally reducing with a reducing agent to remove amino to obtain 1-tetrazole acetate. Compared with the prior art, the method provided by the invention is safer and more environment-friendly, and the obtained product has high yield and purity.
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Paragraph 0027; 0030
(2020/07/21)
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- Production process of 5-aminotetrazole
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The invention belongs to the technical field of chemical synthesis, and particularly discloses a production process of 5-aminotetrazole, which adopts the following synthesis route: aminoguanidine bicarbonate and sulfuric acid are adopted to generate aminoguanidine sulfate; diazotization reaction is carried out on aminoguanidine sulfate and sodium nitrite to generate amidine azide sulfate; and cyclization reaction is performed on the amidine azide sulfate under the action of ammonia water to generate the 5-amino tetrazole. The path is good in safety and few in byproducts; the invention also provides a specific process flow, the process is simple, the operation is easy, and the product yield is high; according to the invention, a high-purity 5-amino tetrazole finished product is obtained bystep-by-step conversion in the diazotization process, control of the addition mode of sodium nitrite and strict control of the temperature and pH in the diazotization and cyclization reaction processes.
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Paragraph 0017-0024
(2021/01/15)
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- Facile synthesis of tetrazolo[1,5-a]pyrimidine with the aid of an effective gallic acid nanomagnetic catalyst
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The present work is the first report of nano-Fe3O4@SiO2-NH-gallic acid in multicomponent reactions as a catalyst. One-pot condensation of various aromatic aldehydes, ?-ketoesters and 5-aminotetrazole to deliver the desired tetrazolo[1,5-a]pyrimidine derivatives is investigated. It involves successful surface modification of Fe3O4@SiO2-NH2 as a potent magnetic support with a well-known natural acid which attracts considerable interests because of its applications in different sciences. This reusable magnetically separable nanocatalyst provides a convenient and reliable method for high yield tetrazole derivatives synthesis in short reaction times with wide variety range of the products and facile isolation. Acid grafting on the surface of amine-functionalized silica-coated magnetic nanoparticles confirmed by Fourier transform infrared (FT-IR) spectroscopy, thermogravimetric analysis (TGA) and energy-dispersive X-ray (EDX) analysis techniques. Structural characterization included scanning electron microscopy (SEM) images along with transmission electron microscopy (TEM) images and vibrating sample magnetometer (VSM) curve applied for morphology and magnetism type determination of the resulted nanocatalyst, respectively.
- Maleki, Ali,Niksefat, Maryam,Rahimi, Jamal,Azadegan, Sepide
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p. 103 - 110
(2019/05/06)
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- Synthesis of 5 - amino tetrazole method
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Synthesis of 5 - amino tetrazole method, in order to hydrazine hydrate, lime nitrogen, sodium nitrite, inorganic acid and inorganic base as the obtained 5 - amino tetrazole. The method through the metathesis reaction, addition reaction and diazo isomerization reaction of the cyano lead lime nitrogen into the aminoguanidine, then generating aminoguandine isomerization reaction to synthesize 5 - amino tetrazole. The invention compared with the traditional method, has the following advantages: (1) price cheap raw materials as the starting raw material, synthetic product is obtained; (2) simplified 5 - amino tetrazole operation process, reduce the reaction solvent types and process the complexity of the operation, reduces the cost of material and production cost, reduces the 5 - amino tetrazole synthesis cost of, improve the market competitiveness of the product. It has high efficiency, high yield, low cost, easy operation and the like.
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Paragraph 0028; 0029; 0030
(2019/06/13)
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- A 5 - substituted four nitrogen azole compound of synthetic method (by machine translation)
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The invention discloses a 5 - substituted four nitrogen azole compound of synthetic method, the synthesis method of the process is as follows: to point pen in the autoclave (I) indicated by the nitrile compounds, sodium azide, nickel ferrite and carboxylic acid ammonium ion exchange resin, added with an organic solvent to the cyclization reaction, the reaction solution after the reaction is finished filter, pickling, desolvation and heavy after crystallization, as shown in formula (II) of the 5 - substituted tetrazole compounds, yield is 85 - 95%, purity ≥ 99%; Formula (I) in the formula (II), the substituent R1 Is phenyl, substituted phenyl, C1 - C3 alkyl or amino; substituted phenyl substituent is methyl, methoxy, F or nitro. The invention of 5 - substituted tetrazole compounds synthesis method, adopt the catalytic ferrous acid nickel and carboxylic acid ammonium ion exchange resin catalyst combination, the carboxylic acid [...], not only good general the reaction substrate, the reaction yield is high, and the catalyst is easily separated and recycled, the production cost is reduced and the three waste emissions. (by machine translation)
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Paragraph 0016; 0017; 0019
(2019/04/04)
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- Cobalt-promoted regioselective preparation of aryl tetrazole amines
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Abstract: A highly general, efficient and simple methodology for the regioselective synthesis of aryl tetrazole amines has been explored. The present method involves consecutive desulphurization and C- N cross-coupling reaction. Cheap, readily available and air stable cobalt catalyst has been used for this methodology. In addition, the substrate scope has been demonstrated. Graphical Abstract: A highly general, efficient and simple methodology for the regioselective synthesis of aryl tetrazole amines has been explored. The present method involves consecutive desulphurization and C- N cross-coupling reaction.
- Lakshmi, Kondraganti,Babu, Manabolu Surendra,Ramachandran, Dittakavi
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- Temperature dependent regioselective synthesis of aryl tetrazole amines using copper source
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One pot highly efficient and simple protocol for the construction of aryl tetrazole amines via desulphurization/substitution/electro cyclization/C-N cross coupling reactions from thiourea with the use of cheap, readily available and air stable copper sour
- Murthy Boddapati,Emmanuel Kola,Kesana, Surendra Babu,Bollikolla, Hari Babu
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p. 177 - 183
(2018/05/09)
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- A novel magnetically recyclable silver-loaded cellulose-based bionanocomposite catalyst for green synthesis of tetrazolo[1,5-a]pyrimidines
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5-Methyl-7-aryl-4,7-dihydrotetrazolo[1,5-a]pyrimidine-6-carboxylic ester derivatives were efficiently synthesized by reaction of methyl or ethyl acetoacetate, 5-aminotetrazole (produced from 2-cyanoguanidine and sodium azide), and various aromatic aldehydes in presence of a new cellulose-based Ag-loaded magnetic bionanostructure. This protocol offers many advantages such as short reaction time, high yield, the remarkable magnetic property of the nanocomposite, and easy separation of the nanocatalyst from the reaction mixture without considerable loss of catalytic activity. Furthermore, X-ray diffraction analysis, field-emission scanning electron microscopy, and energy-dispersive X-ray (EDX) analysis were used to characterize the prepared nanocatalyst.
- Maleki, Ali,Ravaghi, Parisa,Aghaei, Morteza,Movahed, Hamed
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p. 5485 - 5494
(2017/09/23)
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- Production process of 5-amino tetrazole
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The invention relates to a production process of 5-amino tetrazole. 5-amino tetrazole is an important chemical product. The technological process is briefed as the following: adding a certain amount of dicyanodiamide, sodium azide and excess 36.5% hydrochloric acid into a reaction kettle, carrying out condensation reaction under an aqueous phase condition fully to generate 5-amino tetrazole; then performing crystallization separation; using a 30% sodium hydroxide solution to absorb gaseous hydrazoic acid overflowing during crystallization to generate sodium azide for reuse; further conducting centrifugation on the liquid material to separate crystals and a mother solution, and outputting the mother solution as wastewater; dissolving the crystals in water, then conducting further refining to dissolve salt contained in a crude product in water, thus making preparations for the next step separation; carrying out centrifugal separation after dissolving salt in water, separating the product crystals insoluble in water from supernate, outputting the separated supernate as wastewater, drying the product crystals, and generating waste gas during drying.
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Paragraph 0001
(2017/07/19)
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- Zn/MeOH-Mediated Practical and Easy Detritylation of Protected 1-Trityltetrazoles
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A practical and low-cost method for the detritylation of 1-titryltetrazoles using zinc and methanol is described. This procedure is versatile and efficient in the deprotection of several protected tetrazoles bearing aliphatic, aromatic, and heteroaromatic substituents, as well as some functional groups, without decomposition of the tetrazole ring.
- Behloul, Cherif,Bouchelouche, Kenza,Hadji, Yasmine,Benseghir, Saadia,Guijarro, David,Nájera, Carmen,Yus, Miguel
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supporting information
p. 2455 - 2460
(2016/07/28)
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- A 5-amino tetrazole synthesis method (by machine translation)
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The invention relates to a 5-amino tetrazole synthesis method, the raw material ratio of 1:1-1 : 1.5 the dicy and sodium azide and a certain amount of catalyst to high pressure autoclave, then adding solvent, heating to 60-180°C, thermal insulation reaction 1-48 hours; then cooling to room temperature, the exhaust, when the temperature is 60-150°C, vacuum degree is 0.085-0.098 MPa decompression recovering solvent under the condition of; finally used for quality concentration is 10% of hydrochloric acid to adjust the residual liquid pH to 4-5 between, precipitation of the crude product of full cooling, re-filtering, drying to obtain the 5-amino tetrazole. The advantage of this invention lies in: the invention 5-amino tetrazole synthesis method, with cheap dicy as a raw material, occurs and sodium azide [1,3]-dipolar addition generating 5-amino tetrazole, the high-pressure autoclave, to improve the safety of the reaction, it is suitable for industrial production; at the same time, the synthetic product by the method, the product yield can be up to 70% or more. (by machine translation)
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Paragraph 0011
(2016/10/07)
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- Two SrII coordination compounds based on tetrazole-carboxylate ligands
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Two novel coordination compounds, [Sr(atzp)2(H2O)2]·CH3OH (1) and [Sr(dtzpha)(H2O)3]·4H2O (2) [Hatzp=5-aminotetrazole-1-propionic acid, H2dtzpha=1,3-di(tetrazol-5-yl)benzene-N2,N2'-diacetic acid)], have been generated by using 5-aminotetrazole-1-propionic acid and 1,3-di(tetrazol-5-yl)benzene-N2,N2'-diacetic acid to react with strontium salts, respectively. X-ray diffraction analysis reveals that carboxylic groups of two ligands show the same coordination mode (the μ1,1,3-COO coordination mode), compound 1 displays a 1D structure while compound 2 shows a 2D structure, which implies the influence of the number of the carboxylic acid groups. Luminescence properties of 1 and 2 were investigated at room temperature in the solid state.
- Cao, Meng-Jie,Miao, Li-Li,Guo, Meng-Yue,Yang, Gao-Wen,Li, Qiao-Yun
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p. 105 - 111
(2016/10/03)
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- Indium-Mediated Cleavage of the Trityl Group from Protected 1 H -Tetrazoles
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On treatment with indium metal in MeOH-THF, trityl groups undergo reductive removal from 1H-protected tetrazoles (including aliphatic, aromatic, and heteroaromatic substituents), affording the corresponding free tetrazoles in excellent yields, without any decomposition of the tetrazole ring or reduction of any other group.
- Behloul, Cherif,Bouchelouche, Kenza,Guijarro, David,Foubelo, Francisco,Nájera, Carmen,Yus, Miguel
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supporting information
p. 2399 - 2402
(2015/10/19)
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- A novel N-N bond cleavage in 1,5-diaminotetrazole: Synthesis and characterization of 5-picrylamino-1,2,3,4-tetrazole (PAT)
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The reaction of 1,5-diaminotetrazole with picryl chloride (PiCl) forms 5-picrylamino-1,2,3,4-tetrazole (PAT) rather than the expected 1-picrylamino-5-amino-1,2,3,4-tetrazole or 5-picrylamino-1-amino-1,2,3,4- tetrazole. The structure of PAT was confirmed by single-crystal X-ray diffraction. Some of the energetic properties of the synthesized compound were also studied.
- Tang, Yongxing,Yang, Hongwei,Ju, Xuehai,Huang, Hui,Lu, Chunxu,Cheng, Guangbin
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p. 4127 - 4131
(2014/03/21)
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- Detritylation of protected tetrazoles by naphthalene-catalyzed lithiation
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Treatment of N-tritylated tetrazoles bearing aliphatic, aromatic, or heteroaromatic substituents (including functionalized ones) with lithium powder and a catalytic amount of naphthalene led to reductive removal of the trityl group to give excellent yields of the corresponding free tetrazoles without decomposition of the tetrazole ring. The detritylation process was successfully extended to several tetrazoles that are components of sartans, an interesting class of drugs. The chemoselectivity between trityl-tetrazole and trityl-amine bond-cleavage reactions was also studied. This method represents an efficient technique for deprotection of tritylated tetrazoles under non-acidic conditions. Georg Thieme Verlag Stuttgart, New York.
- Behloul, Cherif,Bouchelouche, Kenza,Guijarro, David,Nájera, Carmen,Yus, Miguel
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p. 2065 - 2070
(2014/08/05)
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- Synthesis of nitrogen-rich imidazole, 1,2,4-triazole and tetrazole-based compounds
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Imidazole, 1,2,4-triazole and tetrazole based molecules were prepared for their possible applications in nitrogen-rich gas generators. The energetic salts of 1-(1H-1,2,4-triazol-3-yl)-1H-tetrazole (9), 5-(1H-tetrazol-1-yl)-1H-1,2,4- triazol-3-amine (10), 1-(3-azido-1H-1,2,4-triazol-5-yl)-1H-tetrazole (11) and 3-azido-1H-1,2,4-triazol-5-amine (12) were prepared with various cationic moieties. Their densities, heats of formation, chemical energy of detonation, detonation velocities and pressures were calculated. All of the compounds possessed high positive heats of formation due to high energy contribution from the molecular backbone of the corresponding compounds. The effect of the azole rings and nitro, amino, and azido groups on their physicochemical properties was examined and discussed. The Royal Society of Chemistry 2014.
- Srinivas, Dharavath,Ghule, Vikas D.,Muralidharan, Krishnamurthi
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p. 7041 - 7051
(2014/02/14)
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- Energetic N-trinitroethyl-substituted mono-, Di-, and triaminotetrazoles
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A series of dense energetic N-trinitroethyl-substituted mono-, bis-, and tri-5-aminotetrazoles were obtained by reacting primary amines with in situ generated cyanogen azide, followed by the trinitroethyl functionalization that involves a condensation of a hydroxymethyl intermediate (prepared by a reaction with formaldehyde) with trinitromethane. These compounds were fully characterized by using multinuclear NMR spectroscopy, IR, elemental analysis, differential scanning calorimetry (DSC), and, in one case with 9, with single-crystal XRD analysis. The heats of formation for all compounds were calculated with Gaussian 03 and then combined with experimental densities to determine the detonation pressures (P) and velocities (Dv) of the energetic materials. Interestingly, most of them exhibited high density, good thermal stability, acceptable oxygen balance, positive heat of formation, low impact sensitivity, and excellent detonation properties, which highlighted their practical application potentials as a fascinating class of highly energetic materials.
- Zhang, Qinghua,Zhang, Jiaheng,Parrish, Damon A.,Shreeve, Jean'Ne M.
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p. 11000 - 11006
(2013/09/02)
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- Microwave-assisted synthesis of tetrazolyl pyrazole amides
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A rapid and efficient microwave-assisted synthesis N-(1H-tetrazol-5-yl) derivatives of 3-methyl-1-phenyl-1H-pyrazole- 5-carboxamide is described. These tetrazole pyrazole amides have interesting bacteriocidal, pesticidal, herbicidal and antimicrobial activities. They were identified by IR and 1H NMR elemental analyses. The target compounds were obtained in a shorter reaction time compared to conventional heating methods.
- Hu, Jun,Wang, Jikui,Zhou, Taoyu,Xu, Yanhua
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experimental part
p. 525 - 527
(2011/11/30)
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- Amine salt-catalyzed synthesis of 5-substituted 1H-tetrazoles from nitriles
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The [3+2] cycloaddition reaction between sodium azide and various organic nitriles proceeds smoothly in the presence of amine salts as catalyst in dimethylformamide. The corresponding 5-substituted 1-H tetrazoles were obtained under mild condition in good to excellent yields. Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications to view the free supplemental file. Taylor & Francis Group, LLC.
- Zhou, Yi,Yao, Cheng,Ni, Renjie,Yang, Gaowen
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experimental part
p. 2624 - 2632
(2010/10/03)
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- Bridged piperazine derivatives
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A compound of the formula or the pharmaceutically acceptable salt thereof; wherein a, c, d, k, l, m, W, X, Y Z, R1, and R4 are as defined, and useful to treat inflammation and other immune disorders.
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- Process for producing 5-aminotetrazole
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A process for producing 5-aminotetrazole comprising the steps of: reacting cyanamide with hydrazine in a solvent to form a salt of aminoguanidine; adding thereto an acid and then a nitrite to form a salt of diazoguanidine; and cyclizing the salt of diazoguanidine, upon heating, to thereby produce the 5-aminotetrazole, without isolating the intermediate product and also a process for producing 5-aminotetrazole or a metal salt thereof in the form of powder by spray drying.
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- Blowing agents of tetrazoles and their derivatives
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Disclosed is a novel blowing agent of tetrazoles and their derivatives. The blowing agent comprising tetrazole derivatives is harmless, odorless and inexpensive. Moreover, the agent is low in physical sensitivities and safe in use, and generates clean gas by being sharply decomposed only due to temperature. The blowing agent of tetrazoles and their derivatives employs aminotetrazole derivatives represented by the general formula (1). The blowing agent offers foaming agents for resin molded bodies having good thermal properties, inflators for air bags serving as automobile safety protection, or smoking agents for diffusing chemicals by a low-cost inexpensive synthetic process.
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- 3-Aryl-1-tetrazol-5-yltriazenes, Bench-stable Arenediazonium Ion Synthons: Synthesis of Biaryls and Aryl Halides
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3-Aryl-1-tetrazol-5-yltriazenes have been used as a bench-stable source of diazonium ions for the synthesis of substituted biaryls, aryl halides (iodides, bromides, and chlorides) and azo dyes.The dediazoniation process when induced by trihalogenoacetic acid or acetic acid did not involve free radicals.
- Butler, Richard N.,O'Shea, Paul D.,Shelly, Declan P.
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p. 1039 - 1042
(2007/10/02)
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