Synthetic Protocols and Applications of 1,2,5-Oxadiazoles: A Review DOI
Greesh Kumar, Rajnish Kumar, Avijit Mazumder

et al.

Letters in Organic Chemistry, Journal Year: 2023, Volume and Issue: 21(1), P. 55 - 65

Published: Sept. 11, 2023

Abstract: The 1,2,5-oxadiazole framework has garnered a lot of interest among many nitrogen heterocycles because its capacity to give off NO under physiological circumstances. Because this, major efforts by chemical scientists have been made create novel drug possibilities in medicinal, material, and agriculture science that include the NO-donor N-oxide subunit coupled known or possible pharmacophore C-C/C-N links using suitable spacer. In last few years, derivatives reported as good pharmacophores carbonic anhydrase inhibitors, antibacterial, vasodilating agents, antimalarial, anticancer, etc. presented manuscript, we reviewed granted patents (last 10 years), different synthetic strategies 27 years) 1,2,5- oxadiazoles their synthesis such cycloaddition, dimerization, cyclodehydration, condensation, thermolysis, nitration, oxidation, ring-conversion, These methods also analyzed for merits demerits. manuscript highlighted various applications derivatives. We hope researchers across scientific streams will benefit from review articles designing work related 1,2,5-oxadiazoles.

Language: Английский

Challenging the Limitations of Tetranitro Biimidazole through Introducing a gem-Dinitromethyl Scaffold DOI
Shangbiao Feng,

Baoseng Zhang,

Chunwang Luo

et al.

Organic Letters, Journal Year: 2023, Volume and Issue: 25(8), P. 1290 - 1294

Published: Feb. 16, 2023

A gem-dinitromethyl group was successfully introduced into the TNBI·2H2O structure (TNBI: 4,4′,5,5′-tetranitro-2,2′-bi-1H-imidazole) to obtain 1-(dinitromethyl)-4,4′,5,5′-tetranitro-1H,1′H-2,2′-biimidazole (DNM-TNBI). Benefiting from transformation of an N-H proton a group, current limitations TNBI were well solved. More importantly, DNM-TNBI has high density (1.92 g·cm–3, 298 K), good oxygen balance (15.3%), and excellent detonation properties (Dv = 9102 m·s–1, P 37.6 GPa), suggesting that it great potential as oxidizer or high-performance energetic material.

Language: Английский

Citations

24
High-energy hydroxytetrazoles: Design, synthesis and performance DOI Creative Commons
Alexander А. Larin, Леонид Л. Ферштат

Energetic Materials Frontiers, Journal Year: 2021, Volume and Issue: 2(1), P. 3 - 13

Published: Jan. 14, 2021

In recent years, the development of novel advanced high-energy density materials has significantly shifted toward nitrogen-containing heterocyclic derivatives, which demonstrate a great potential for multipurpose application patterns. Among known heterocycles hydroxytetrazole is special importance due to its high nitrogen-oxygen content and possibility serve as anion counterpart form diverse array organic inorganic energetic salts. this review, we summarized main achievements on synthesis performance hydroxytetrazole-based materials. Potential applications presented compounds their environmental compatibility are especially emphasized.

Language: Английский

Citations

55
Design and Synthesis of Nitrogen‐Rich Azo‐Bridged Furoxanylazoles as High‐Performance Energetic Materials DOI
Alexander А. Larin, Alexander V. Shaferov, Alexander S. Kulikov

et al.

Chemistry - A European Journal, Journal Year: 2021, Volume and Issue: 27(59), P. 14628 - 14637

Published: July 29, 2021

A series of novel energetic materials comprising azo-bridged furoxanylazoles enriched with functionalities was designed and synthesized. These high-energy were thoroughly characterized by IR multinuclear NMR (1 H, 13 C, 14 N) spectroscopy, high-resolution mass spectrometry, elemental analysis, differential scanning calorimetry (DSC). The molecular structures representative amino azo oxadiazole assemblies additionally confirmed single-crystal X-ray diffraction powder diffraction. comparison contributions explosophoric moieties into the density revealed that furoxan 1,2,4-oxadiazole rings are densest motifs while substitution azide fragments on nitro ones leads to an increase density. Azo bridged have high nitrogen-oxygen contents (68.8-76.9 %) thermal stability. synthesized compounds exhibit good experimental densities (1.62-1.88 g cm-3 ), very enthalpies formation (846-1720 kJ mol-1 and, as a result, excellent detonation performance (detonation velocities 7.66-9.09 km s-1 pressures 25.0-37.7 GPa). From application perspective, parameters exceed those benchmark explosive RDX, combination acceptable friction sensitivity azo(1,2,4-triazolylfuroxan) make it promising potential alternative PETN.

Language: Английский

Citations

35
Energetic isomers of bridged oxadiazole nitramines: the effect of asymmetric heterocyclics on stability and energetic properties DOI
Sicheng Liao, Tianlin Liu, Zhiyu Zhou

et al.

Dalton Transactions, Journal Year: 2021, Volume and Issue: 50(38), P. 13286 - 13293

Published: Jan. 1, 2021

A series of asymmetric oxadiazole nitramine compounds were designed and synthesized, a comparative study detonation, sensitivity, thermal properties three isomers is made.

Language: Английский

Citations

33
Review on the Synthesis and Performance for 1,3,4‐Oxadiazole‐Based Energetic Materials DOI
Yao Du,

Zhongkai Qu,

Huan‐Chün Wang

et al.

Propellants Explosives Pyrotechnics, Journal Year: 2021, Volume and Issue: 46(6), P. 860 - 874

Published: April 23, 2021

Abstract Energetic materials have been widely used in both military and civilian fields. The development of new high‐energy with improved performance enhanced stability is critical for promoting future space applications. Recently, researchers the field energetic paid significant attention to oxadiazole‐based compounds, among which 1,3,4‐oxadiazole demonstrates moderate energy levels better stability, owing absence readily cleaved N−O bonds compared other oxadiazole isomers, such as 1,2,4‐oxadiazole 1,2,5‐oxadiazole. Therefore, an exceptional explosophoric motif efficient compromise between several outstanding achieved based on combination units various functional groups or rings, polynitrobenzene, furazan, pyrazole, itself. This review provides overview 1,3,4‐oxadiazole‐based during past few years, outlines their synthesis performance, contrasts them conventional materials. Owing convenience synthetic routes excellent properties, skeleton may be considered next‐generation high‐performance specifically heat‐resistant explosives insensitive explosives.

Language: Английский

Citations

25
Molecular Packing Density Coefficient Contradiction of High-Density Energetic Compounds and a Strategy to Achieve High Packing Density DOI

Fucheng Bao,

Ying Xiong, Rufang Peng

et al.

Crystal Growth & Design, Journal Year: 2022, Volume and Issue: 22(5), P. 3252 - 3263

Published: April 21, 2022

High packing density (dc) is of great importance in the field energetic materials, as it positively correlated with energy performances, which refer to power, detonation property, or specific kinetic a cylinder. This makes high dc focus for designing new molecules. article systematically analyzes composition, molecular topology, intermolecular interaction, molecule (dm), and coefficient (PC) top 36 highest (≥1.90 g/cm3) CHNO compounds extracted from CSD. For these compounds, dm–PC contradiction exists. dm increases, PC decreases. The absence planar structure strong hydrogen bonding acceptor donor high-dm molecules responsible low contradiction. Two strategies are summarized achieving dc: first, design caged oxygen balance because they generally possess extraordinarily remedy shortcoming rather PC, other dense acceptors donors obtain PCs further based on moderate dm. introduction NH2 needs be emphasized second strategy. work expected guide high-density compounds.

Language: Английский

Citations

18
Theoretical study of friction sensitivity of energetic materials DOI
Hongyan Li, Wei Zeng,

Fusheng Liu

et al.

Journal of Physics and Chemistry of Solids, Journal Year: 2025, Volume and Issue: unknown, P. 112692 - 112692

Published: March 1, 2025

Language: Английский

Citations

0
A strategy for stabilizing of N8 type energetic materials by introducing 4-Nitro-1,2,3-Triazole scaffolds DOI
Shangbiao Feng, Yunlu Li, Qi Lai

et al.

Chemical Engineering Journal, Journal Year: 2021, Volume and Issue: 430, P. 133181 - 133181

Published: Oct. 25, 2021

Language: Английский

Citations

22
Relationship between the Molecular Structure and Stacking Mode: Characteristics of the D2h and D3h Molecules in Planar Layer-Stacked Crystals DOI
Rupeng Bu, Guangrui Liu, Kai Zhong

et al.

Crystal Growth & Design, Journal Year: 2021, Volume and Issue: 21(12), P. 6847 - 6861

Published: Nov. 16, 2021

The molecular structure and stacking mode relationship is the core of creating planar layer-stacked materials by crystal engineering. However, it remains highly challenging to clarify relationship. By exhaustively extracting 50 compounds with D2h or D3h point groups from Cambridge Structural Database, we study in this work, characteristics molecules those others for comparison. For a hydrogenous molecule, requires both strong donor acceptor hydrogen bonds (HBs) therein large positive negative electrostatic potential extremes (e.g., ≥35 kcal/mol at theoretical level B3LYP/6-311G(d)) situated on its edge layer stacking, while regarding H free stacked layers, they are prone be sparsely arranged, intralayer intermolecular interactions belong weak halogen bonding other van der Waals attraction, rather small their edges and/or faces. Additionally, first propose definitions six types modes scientifically exactly classify them based relative orientations arrangement planes crystal. Accordingly, strategy constructing HBs proposed. This work expected benefit engineering materials.

Language: Английский

Citations

21
Multisubstituted Imidazolo[4,5-d]pyridazine Fused Ring System Resulting from Nitroamine–Nitroimine Tautomerism DOI
Lu Hu, Chunlin He, Siping Pang

et al.

Organic Letters, Journal Year: 2021, Volume and Issue: 23(20), P. 7860 - 7864

Published: Sept. 30, 2021

A series of multisubstituted imidazolo[4,5-d]pyridazine fused ring compounds was synthesized in which nitroamine–nitroimine tautomerism is exhibited. The electrostatic potential indicates that the nitroimino group has lowest negative value, second only to nitro group, culminating nitroamino area, highest positive value. In addition, a strong hydrogen bond system arises from newly formed tautomer suggests more stable than its analogue.

Language: Английский

Citations

17