This review highlights recent developments in the synthesis and application of furoxan. The chemistry of furoxan is relatively underdeveloped compared to that of other heterocycles owing to its difficult synthesis, which is ascribed to the labile nature of this molecule under various reaction conditions. Nevertheless, recent studies have conducted a variety of bond-forming reactions on the furoxan ring a post-ring introduction of substituents (PRIS) strategy. This strategy enables the synthesis of furoxan molecules of interest more directly than the conventional methods that rely on the pre-installation of substituents on the furoxan ring precursors. In this review, the PRIS strategy for furoxan synthesis is classified and discussed according to the type of bond formed. Additionally, recent progress in the application of furoxan molecules, predominantly facilitated by the development of new synthetic methods, is covered in this review.
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http://dx.doi.org/10.1039/d3ra00189j | DOI Listing |
The synthesis and characterization of low-melting-point insensitive energetic materials are crucial due to their increasing applications in melt-cast explosives. In this work, a furazan-derived energetic compound, 3,4-bis[3(2-azidoethoxy)furazan-4-yl]furoxan (DAeTF), exhibiting insensitive and high-energy characteristics, is rationally designed and synthesized. The structure of DAeTF is characterized by nuclear magnetic resonance spectroscopy, Fourier transform infrared spectroscopy, elemental analysis, mass spectrometry, and single-crystal X-ray diffraction.
View Article and Find Full Text PDFPharmaceutics
September 2024
Xinjiang Key Laboratory of Natural Medicines Active Components and Drug Release Technology, Ministry of Education, Engineering Research Center of Xinjiang and Central Asian Medicine Resources, College of Pharmacy, Xinjiang Medical University, Urumqi 830017, China.
Beilstein J Org Chem
September 2024
N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 119991, Leninsky Prospect, 47, Moscow, Russian Federation.
A straightforward protocol for the synthesis of a previously unknown [1,2,5]oxadiazolo[3,4-][1,2,3]triazin-7(6)-one heterocyclic system was developed. The described approach is based on tandem diazotization/azo coupling reactions of (1,2,5-oxadiazolyl)carboxamide derivatives bearing both aromatic and aliphatic substituents. The NO-donor ability of the synthesized furoxano[3,4-][1,2,3]triazin-7(6)-ones was additionally evaluated.
View Article and Find Full Text PDFJ Org Chem
April 2024
School of Materials Science & Engineering, Beijing Institute of Technology, Beijing 100081, China.
Energetic compounds that display high thermal stability and insensitivity properties are essential for applications in mining, gas drilling, etc. In this work, a novel 4-nitro-5-aminoisoxazole energetic moiety oriented to enhance thermal stability and decrease the sensitivity of furazan/furoxan analogues was constructed. The generation of a vicinal amino-nitro structure can be effectively realized in one step by a green and mild ring-closing reaction of nitroacetonitrile potassium salt with chloroxime in aqueous solution.
View Article and Find Full Text PDFPhys Chem Chem Phys
March 2024
High-Tech Institute of Xi'an, Xi'an 710025, China.
3,4-Bis(3-nitrofurazan-4-yl)furoxan (DNTF) is a novel energetic material with an excellent performance and has attracted considerable attention. Motivated by recent theories and experiments, we had carried out experimental and theoretical studies on the high-pressure responses of vibrational characteristics, in conjunction with structural and electronic characteristics. It is found that all observed infrared spectra peaks seem to shift towards higher frequencies.
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