Tandem acid-promoted intramolecular azide-hydrazone electrocyclization/hydrolysis approach for the synthesis of N-Aminotetrazoles

Titenkova, Kseniia Yu; Shaferov, Alexander V.; Larin, Alexander А.; Epishina, Margarita A.; Ananyev, Ivan V.; Ферштат, Леонид Л.

doi:10.1016/j.tet.2021.132563

Cited by 4 publications

(2 citation statements)

References 61 publications

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“…The Due to the invisibility of the missing nitrogen atoms, proton coupled 15 N NMR measurement (Figure 2) was performed. The resonances for the azide at δ = À 302.1 (N α ), À 158.9 (N γ ), and À 136.3 (N β ) are in the same range as comparable azido-methyl compounds.…”

Section: Nmr Spectroscopymentioning

confidence: 99%

“…While the tetrazole moiety, with its high nitrogen content, has been introduced in several recent high-performing energetic materials [8][9][10][11][12][13][14] as well as potential pharmaceuticals [15][16][17] several 1 N-functionalised tetrazoles [18] such as 1-methyl-5Htetrazole [19] (1-MTZ) and 1-amino-5H-tetrazole [20] (1-AT) promoted the range of adjustability of energetic properties of ECCs. 1-MTZ is able to stabilize sensitive materials (e. g., AgCNO), thus performs well when desensitizing an energetic coordination compound, whereas 1-AT drastically increases the sensitivity.…”

Section: Introductionmentioning

confidence: 99%

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1‐(Azidomethyl)‐5H‐Tetrazole: A Powerful New Ligand for Highly Energetic Coordination Compounds

Kofen

Lommel

Wurzenberger

et al. 2022

Chemistry A European J

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Highly energetic 1‐(azidomethyl)‐5H‐tetrazole (AzMT, 3) has been synthesized and characterized. This completes the series of 1‐(azidoalkyl)‐5H‐tetrazoles represented by 1‐(azidoethyl)‐5H‐tetrazole (AET) and 1‐(azidopropyl)‐5H‐tetrazole (APT). AzMT was thoroughly analyzed by single‐crystal X‐ray diffraction experiments, elemental analysis, IR spectroscopy and multinuclear (1H, 13C, 14N, 15N) NMR measurements. Several energetic coordination compounds (ECCs) of 3d metals (Mn, Fe, Cu, Zn) and silver in combination with anions such as (per)chlorate, mono‐ and dihydroxy‐trinitrophenolate were prepared, giving insight into the coordination behavior of AzMT as a ligand. The synthesized ECCs were also analyzed by X‐ray diffraction experiments, elemental analysis, and IR spectroscopy. Differential thermal analysis for all compounds was conducted, and the sensitivity towards external stimuli (impact, friction, and ESD) was measured. Due to the high enthalpy of formation of AzMT (+654.5 kJ mol−1), some of the resulting coordination compounds are extremely sensitive, yet are able to undergo deflagration‐to‐detonation transition (DDT) and initiate pentaerythritol tetranitrate (PETN). Therefore, they are to be ranked as primary explosives.

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Section: Nmr Spectroscopymentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

1‐(Azidomethyl)‐5H‐Tetrazole: A Powerful New Ligand for Highly Energetic Coordination Compounds

Kofen

Lommel

Wurzenberger

et al. 2022

Chemistry A European J

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Five-membered ring systems: with more than one N atom

Yet

2023

Progress in Heterocyclic Chemistry

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Revisiting the Synthesis of Functionally Substituted 1,4-Dihydrobenzo[e][1,2,4]triazines

Epishina

Ферштат

2022

Molecules

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A series of novel 1,4-dihydrobenzo[1,2,4][e]triazines bearing an acetyl or ester moiety as a functional group at the C(3) atom of the 1,2,4-triazine ring were synthesized. The synthetic protocol is based on an oxidative cyclization of functionally substituted amidrazones in the presence of DBU and Pd/C. It was found that the developed approach is suitable for the preparation of 1,4-dihydrobenzo[e][1,2,4]triazines, but the corresponding Blatter radicals were isolated only in few cases. In addition, a previously unknown dihydrobenzo[e][1,2,4]triazolo[3,4-c][1,2,4]triazine tricyclic open-shell derivative was prepared. Studies of thermal behavior of the synthesized 1,4-dihydrobenzo[1,2,4][e]triazines revealed their high thermal stability (up to 240–250 °C), which enables their application potential as components of functional organic materials.

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Tandem acid-promoted intramolecular azide-hydrazone electrocyclization/hydrolysis approach for the synthesis of N-Aminotetrazoles

Cited by 4 publications

References 61 publications

1‐(Azidomethyl)‐5H‐Tetrazole: A Powerful New Ligand for Highly Energetic Coordination Compounds

1‐(Azidomethyl)‐5H‐Tetrazole: A Powerful New Ligand for Highly Energetic Coordination Compounds

Five-membered ring systems: with more than one N atom

Revisiting the Synthesis of Functionally Substituted 1,4-Dihydrobenzo[e][1,2,4]triazines

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