Synthetic Routes to a Triazole and Tetrazole with Trinitroalkyl Substitution at Nitrogen

Klapötke, Thomas M.; Krumm, Burkhard; Reith, Thomas; Unger, Cornelia C.

doi:10.1021/acs.joc.8b01072

Cited by 18 publications

(6 citation statements)

References 28 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A large variety of pyrimidine modified tetrazole and azido derivatives (Table and ) are prepared from relevant reactants producing a high yield. The general conditions and expected products of the reaction is shown in Scheme …”

Section: Resultsmentioning

confidence: 99%

Tetrazole and Azido Derivatives of Pyrimidine: Synthesis, Mechanism, Thermal Behaviour & Steering of Azido–Tetrazole Equilibrium

et al. 2020

View full text Add to dashboard Cite

A new family of pyrimidine modified tetrazole & azido derivatives (1-16) was developed using the conventional and nucleophilic substitution methods. The 1H-tetrazol-1-yl)pyrimidine (1-10) compounds were prepared via traditional cycloaddition and condensation method. The compounds tetrazolo [1,5-a]pyrimidine (11 a,12 a, and 13 a), azido-(1H-tetrazol-1-yl) pyrimidine (14 a and 15 a) and tetrazolo[1,5-c]pyrimidine (16 a) were synthesized by simultaneously introducing conventional and nucleophilic substitution approaches. The latter technique was easy to process and reduce the synthesis time. The factors (solvent, temperature, steric effect, electron-donating groups, and electron-withdrawing groups) were found responsible for steering the azido-tetrazole equilibrium in the compounds 11 a, 12 a, 13 a, and 16 a. All the prepared compounds were well characterized including single-crystal X-ray diffraction struc- tures of 1, 3, 4, 6, 8, 10, 11 a, 12 a, 13 a, 14 a, 15 a, and 16 a. Thermal behaviour was investigated by differential scanning calorimetry (DSC) and thermal gravimetric analysis (TGA). The current work is significant to the development of a new class of pyrimidine modified tetrazole and azido derivatives in sense of easy reaction approach, good to excellent yields, safe process, and simple work-ups.

show abstract

Section: Resultsmentioning

confidence: 99%

Tetrazole and Azido Derivatives of Pyrimidine: Synthesis, Mechanism, Thermal Behaviour & Steering of Azido–Tetrazole Equilibrium

et al. 2020

View full text Add to dashboard Cite

show abstract

“…Nitraminodiacetic acid diethyl ester was synthesized according to literature procedures. , The ester (1.00 g, 4.27 mmol) was suspended in hydrochloric acid (37%, 25 mL) and then refluxed for 6 h. After evaporating the solvent, nitraminodiacetic acid was obtained in quantitative yield as a colorless solid.…”

Section: Methodsmentioning

confidence: 99%

Oxygen-Rich Bis(trinitroethyl esters): Suitable Oxidizers as Potential Ammonium Perchlorate Replacements

et al. 2020

Self Cite

View full text Add to dashboard Cite

In the area of solid rocket propellants, research efforts are ongoing to find suitable oxidizers as ammonium perchlorate (AP) replacements. On the one hand, AP's performance data are excellent; on the other hand, AP and its combustion products lead to health and environmental issues. Herein, the nitraminodiacetic acid bis(2,2,2-trinitroethyl ester) (NABTNE) is presented as a green AP alternative and is compared to the bis(trinitroethyl ester) of malonic acid (MaBTNE). Simple syntheses based on economic starting materials furnished both compounds, with NABTNE having a positive oxygen balance (according to CO), a density of 1.84 g cm −3 (@T = −118 °C), and a decomposition point of 180 °C. The density of MaBTNE (δ = 1.81 g cm −3 @T = −147 °C) and the thermal stability (T dec = 157 °C) are also advantageous. NABTNE as a moderately sensitive and the most promising derivative was shown to be of good stability toward long-term storage. Moreover, mixtures for a potential application in solid rocket formulations were calculated using EXPLO5 (V 6.03).

show abstract

“…This moiety is useful to improve the overall performance of an energetic compound by enhancing the density and oxygen balance [ 5 , 6 ]. Several methods have been used to synthesize trinitromethyl-based heterocyclic compounds by nitrating dinitromethyl, ethyl acetate, or an acetonyl group [ 7 , 8 , 9 , 10 ]. Subsequently, several trinitromethyl heterocyclic compounds with excellent properties were developed based on those methods [ 11 , 12 , 13 , 14 ].…”

Section: Introductionmentioning

confidence: 99%

Boosting the Energetic Performance of Trinitromethyl-1,2,4-oxadiazole Moiety by Increasing Nitrogen-Oxygen in the Bridge

Chen

Dou

et al. 2022

IJMS

View full text Add to dashboard Cite

The trinitromethyl moiety is a useful group for the design and development of novel energetic compounds with high nitrogen and oxygen content. In this work, by using an improved nitration method, the dinitromethyl precursor was successfully nitrated to the trinitromethyl product (2), and its structure was thoroughly characterized by FTIR, NMR, elemental analysis, differential scanning calorimetry, and single-crystal X-ray diffraction. Compound 2 has a high density (1.897 g cm−3), high heat of formation (984.8 kJ mmol−1), and a high detonation performance (D: 9351 m s−1, P: 37.46 GPa) that may find useful applications in the field of high energy density materials.

show abstract

Synthetic Routes to a Triazole and Tetrazole with Trinitroalkyl Substitution at Nitrogen

Cited by 18 publications

References 28 publications

Tetrazole and Azido Derivatives of Pyrimidine: Synthesis, Mechanism, Thermal Behaviour & Steering of Azido–Tetrazole Equilibrium

Tetrazole and Azido Derivatives of Pyrimidine: Synthesis, Mechanism, Thermal Behaviour & Steering of Azido–Tetrazole Equilibrium

Oxygen-Rich Bis(trinitroethyl esters): Suitable Oxidizers as Potential Ammonium Perchlorate Replacements

Boosting the Energetic Performance of Trinitromethyl-1,2,4-oxadiazole Moiety by Increasing Nitrogen-Oxygen in the Bridge

Contact Info

Product

Resources

About