14213-10-6Relevant academic research and scientific papers
Azasydnone-novel "green" building block for designing high energetic compounds
Dalinger, Igor L.,Serushkina, Olga V.,Muravyev, Nikita V.,Meerov, Dmitry B.,Miroshnichenko, Evgeniy A.,Kon'Kova, Tatyana S.,Suponitsky, Kyrill Yu.,Vener, Mikhail V.,Sheremetev, Aleksei B.
, p. 18669 - 18676 (2018)
The discovery of novel explosophoric building blocks for the construction of energetic compounds is extremely rare. Here, based on the comparative experimental properties and computational analysis of compounds where nitroaryl backbones were bonded with various nitrogen/oxygen-rich groups, it is shown that compounds having the azasydnone group possess higher density, detonation performance and thermal stability than their corresponding nitro, azido and tetrazole-analogs. All of these properties, as well as the oxygen balanced content of the "green" nitrogen rich endothermic unit make them an attractive explosophoric building block in the field of energetic materials chemistry.
Oxidation/ MCR domino protocol for direct transformation of methyl benzene, alcohol, and nitro compounds to the corresponding tetrazole using a three-functional redox catalytic system bearing TEMPO/Co(III)-porphyrin/ Ni(II) complex
Mahmoudi, Boshra,Rostami, Amin,Kazemnejadi, Milad,Hamah-Ameen, Baram Ahmed
, (2020/12/21)
A redox catalytic system for oxidation-reduction reactions and the domino preparation of tetrazole compounds from nitro and alcohol precursors was designed, prepared and characterized by UV–vis, GPC, TGA, XRD, EDX, XPS, VSM, FE-SEM, TEM, DLS, BET, NMR, and ICP analyses. The catalyst was prepared via several successive steps by demetalation of chlorophyll b, copolymerization with acrylated TEMPO monomers, complexation with Ni and Co metals (In two different steps), then immobilized on magnetic nanoparticles. The presence of three functional groups including TEMPO, coordinated cobalt, and coordinated nickel in the catalyst, allowed the oxidation of various types of alcohols, alkyl benzenes as well as the reduction of nitro compounds by a single catalyst. All reactions yielded up to 97 % selectivity for oxidation and reduction reactions. Next, the ability of the catalyst to successfully convert alcohol, methyl benzenes and nitro to their corresponding tetrazoles was studied.
Five-membered N-Heterocycles Synthesis Catalyzed by Nano-silica Supported Copper(II)–2-imino-1,2-diphenylethan-1-ol Complex
Sharghi, Hashem,Shiri, Pezhman,Aberi, Mahdi
, p. 2844 - 2862 (2017/09/25)
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.]
Synthetic manifestation of nitro substituted tetrazole-N-(hetero)aryl derivatives and energetic studies
Kommu, Nagarjuna,Balaraju,Ghule, Vikas D.,Sahoo, Akhila K.
supporting information, p. 7366 - 7371 (2017/04/26)
A workable cost-efficient synthetic method for the construction of nitro substituted tetrazole-N-aryl/heteroaryl derivatives is discussed here. The energetic functional groups-NO2,-NHNO2 and-N3 are reliably inserted into the molecular backbone, making the tetrazole-N-aryl derivatives highly energetic and insensitive to heat and impact. For example, the tetrazole derivatives 7 and 8, bearing a-NO2 or a-NHNO2 group, exhibit energetic properties close to RDX, but with enhanced insensitivity. Most of the synthesized compounds show exothermic decomposition and are consequently useful for energetic material applications.
Trifluoromethanesulfonimide catalysed synthesis of 1-substituted-1H-1,2,3,4-tetrazoles using glycerol as green solvent at room temperature
Wang, Hongshe,Wei, Fenyan,Chen, Qi,Hu, Xiaobing,Niu, Xiaomei
, p. 570 - 572 (2016/10/05)
A direct synthetic protocol is developed for the synthesis of 1-substituted-1H-1,2,3,4-tetrazoles via a three-component condensation of primary amines, triethyl orthoformate and sodium azide in the presence of 5 mol% of trifluoromethanesulfonimide (HNTf2) in glycerol at room temperature with good to excellent yields.
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
Karimi Zarchi, Mohammad Ali,Nazem, Fatemeh
, p. 91 - 99 (2014/01/23)
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.
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
Sharghi, Hashem,Ebrahimpourmoghaddam, Sakineh,Doroodmand, Mohammad Mahdi
, p. 41 - 48 (2013/07/05)
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.
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]
Aridoss, Gopalakrishnan,Laali, Kenneth K.
experimental part, p. 2827 - 2835 (2011/06/23)
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.
Synthesis and transformations of 1-(azidophenyl)-1H-tetrazoles
Pokhodylo,Matiichuk,Obushak
experimental part, p. 556 - 560 (2010/08/20)
Diazotization of 1-(aminophenyl)-1H-tetrazoles and subsequent treatment of the diazonium salts with sodium azide gave 1-(azidophenyl)-1H-tetrazoles which were brought into cyclization with ethyl acetoacetate and cyanoacetanilide to obtain 1,2,3-triazole derivatives. Under these conditions, the tetrazole ring may undergo cleavage with formation of cyanamide group.
Indium triflate-catalyzed one-pot synthesis of 1-substituted-1H-1,2,3,4-tetrazoles under solvent-free conditions
Kundu, Dhiman,Majee, Adinath,Hajra, Alakananda
experimental part, p. 2668 - 2670 (2009/08/09)
A simple, efficient, and general method has been developed for the synthesis of 1-substituted-1H-1,2,3,4-tetrazoles via a three-component condensation of amine, trimethyl orthoformate, and sodium azide in presence of a catalytic amount of indium triflate
