Gem-dinitro compounds in organic synthesis. 4. Use of the condensation product of glyoxal and dinitromethane in the synthesis of nitro-1,2,3-triazoles

Baryshnikov, A. T.; Erashko, V. I.; Zubanova, N. I.; Уграк, Б. И.; Шевелев, С. А.; Fainzil'berg, A. A.; Семенов, В. В.

doi:10.1007/bf00863589

Cited by 10 publications

(10 citation statements)

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“…[6] However, unlike the reported colorless or light-brown crystals, we obtained 4 as a sticky product that is hygroscopic. Diammonium 4,4'-bis(5-nitro-1,2,3-2H-triazolate) (5), the precursor for methylation, amination, and N-oxidization reactions, was realized by bubbling gaseous ammonia through a diethyl ether solution of 4 for five minutes and then removing the solvent under vacuum.…”

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confidence: 62%

“…As far as we know, only compound 4 and its potassium salt have been previously reported, and the properties of 4 and its derivatives are still unknown. [6] It was also worthwhile to investigate the influence of the substituted position in the 4,4'-bis(5-nitro-1,2,3-2H-triazole) system, on detonation properties. Herein, we report the synthesis and the characterization of 4 with a variety of functionalized derivatives; methylation, amination, and N-oxidation strategies were employed to develop more powerful, less sensitive, and eco-friendly energetic materials.…”

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confidence: 99%

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Energetic Materials with Promising Properties: Synthesis and Characterization of 4,4′‐Bis(5‐nitro‐1,2,3‐2H‐triazole) Derivatives

Shreeve

2015

Angew Chem Int Ed

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Using a variety of functionalization strategies, derivatives of 4, 4'-bis(5-nitro-1,2,3-2H-triazole) were designed, synthesized, and characterized. The isomers were separated, their structures were confirmed with single-crystal X-ray analysis, and their properties were determined by differential scanning calorimetry, density, impact sensitivity, heat of formation, and detonation velocity and pressure (calculated by EXPLO5 V6.01). Those materials were found to exhibit superior detonation performance when compared with the other fully carbon-nitrated bis(azoles).

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confidence: 62%

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confidence: 99%

Energetic Materials with Promising Properties: Synthesis and Characterization of 4,4′‐Bis(5‐nitro‐1,2,3‐2H‐triazole) Derivatives

Shreeve

2015

Angew Chem Int Ed

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“…In this case heterocyclization is accompanied by the elimination of one of the nitro groups [11,31,32]. In the opinion of the authors the reaction of dinitroalkenes with sodium azide takes place as a two-stage intramolecular cyclization.…”

Section: Ch Chmentioning

confidence: 99%

“…The esters of dinitroacetic acid 30 and various derivatives of 1,1-dinitro-and 1,1,1-trinitroalkanes 31 were used as initial gem-dinitroethenes [11]. A similar approach was used in the synthesis of bis(4-nitro-1,2,3-triazol-5-yl) (32) by the reaction of the diacetate of 1,1,4,4-tetranitrobutane-2,3-diol (33) In the opinion of the authors the reaction takes place through the formation of the intermediate tetranitrobutadiene [31]. In contrast to the diacetate, in reaction with sodium azide in methanol the monoacetate of tetranitrobutanediol (34) forms 5-substituted 4-nitro-1,2,3-triazole, which the authors oxidized with potassium permanganate without isolation to 5-nitro-1,2,3-triazole-4-carboxylic acid (35).…”

Section: Ch Chmentioning

confidence: 99%

Synthesis and properties of nitro-1,2,3-triazoles (Review)

Vereschagin

Pokatilov

Kizhnyaev

2008

Chem Heterocycl Comp

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Published data on methods for the synthesis of substituted 4(5)-nitro-1,2,3-triazoles and their properties are reviewed.Against the background of the extremely large amount of published information about methods for the production of vicinal triazoles and their properties the chemistry of nitro-substituted triazoles of this series is in an embryonic state. At the same time, according to existing data, vicinal nitrotriazoles may find use in the synthesis of medicines, dyes, agents for the struggle against agricultural pests, energy-rich components of propellants, special-purpose powders, and in other regions of technology. However, the practical application of these compounds has been restrained by the lack of technologically convenient methods for their production. Until now sufficiently effective preparative methods have not been developed for their synthesis. With respect to their properties it is known only that the nitro group of the triazoles is capable of being reduced catalytically to an amino group and substituted by various nucleophilic fragments, while the triazole ring is alkylated by alkyl halides and adds to an activated multiple bond. The limited information is probably explained by the poor availability of vicinal nitrotriazoles, which is most likely due to the passivity of the 1,2,3-triazole in electrophilic substitution reactions at carbon atoms and particularly in nitration processes. In this connection it seems expedient to examine methods for the synthesis of nitro-substituted 1,2,3-triazoles by direct nitration with due regard to the conditions determining the entry of the nitro group into the azole ring and also methods for the construction of nitrotriazoles by the cyclization of open-chain nitro compounds and to assess their properties. SYNTHESIS OF NITRO-1,2,3-TRIAZOLES Nitration of 1,2,3-TriazolesThe inertness of the carbon atoms of the triazole ring toward electrophilic reagents is due to distribution of the electron density of the ring in such a way that the carbon atoms carry a partial positive charge, preventing the addition of a nitronium cation. Therefore, the path to direct nitration of the ring of unsubstituted vicinal triazole has not so far been realized. Attempts to introduce a nitro group into the ring of the heterocycle of 1-phenyl-and 4-phenyl-1,2,3-triazoles were unsuccessful. 1-Phenyl-1,2,3-triazole (1) does not form 4(5)-nitrosubstituted triazole during nitration even under rigid conditions. Here, only the phenyl ring is nitrated-initially at the para position and then at the ortho position [1-3].

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“…Baryshnikov et al [6] have synthesized several 4-nitro-1,2,3-triazoles by reacting sodium azide with a variety of 1,1-dinitroethylene synthons. He also reported the synthesis of 5,5 0 -dinitro-4,4 0 -bi-1,2,3-triazole [7]. Myachina et al [8] reported 2-phenyl-1,2,3-triazole by the cyclization of glyoxal phenylosazone.…”

Section: Introductionmentioning

confidence: 95%

Theoretical studies on a series of 1,2,3-triazoles derivatives as potential high energy density compounds

Zhang

2011

Struct Chem

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Based on the full-optimized molecular geometric structures at B3LYP/6-31G* and B3P86/6-31G* levels, the densities (q), detonation velocities (D), and pressures (P) for a series of 1,2,3-triazole derivatives, as well as their thermal stabilities, were investigated to look for high energy density compounds (HEDCs). The heats of formation (HOFs) are also calculated via designed isodesmic reactions. The calculations on the bond dissociation energies (BDEs) indicate that the BDEs of the initial scission step are between 53 and 70 kcal/mol, and 4-nitro-1,2,3-triazole is the most reactive compound, while 1-(2 0 ,4 0 -dinitrophenyl)-5-nitro-1,2,3-triazole is the least reactive compound for 1,2,3-triazole derivatives studied. The condensed phase heats of formation are also calculated for the title compounds. These results would provide basic information for the further studies of HEDCs. The detonation data of 1-(3 0 ,4 0 -dinitrophenyl)-4-nitro-1,2,3-triazole and 1-(2 0 ,4 0 -dinitrophenyl)-4-nitro-1,2,3-triazole show that they meet the requirement for HEDCs.

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Gem-dinitro compounds in organic synthesis. 4. Use of the condensation product of glyoxal and dinitromethane in the synthesis of nitro-1,2,3-triazoles

Cited by 10 publications

References 1 publication

Energetic Materials with Promising Properties: Synthesis and Characterization of 4,4′‐Bis(5‐nitro‐1,2,3‐2H‐triazole) Derivatives

Energetic Materials with Promising Properties: Synthesis and Characterization of 4,4′‐Bis(5‐nitro‐1,2,3‐2H‐triazole) Derivatives

Synthesis and properties of nitro-1,2,3-triazoles (Review)

Theoretical studies on a series of 1,2,3-triazoles derivatives as potential high energy density compounds

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