5-Nitrotetrazol and 1,2,4-Oxadiazole Methylene-Bridged Energetic Compounds: Synthesis, Crystal Structures and Performances

Zhang, Jiarong; Bi, Fuqiang; Yang, Zhi; Xue, Qunji; Wang, Bozhou

doi:10.3390/molecules26237072

Cited by 5 publications

(1 citation statement)

References 31 publications

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“…Wang et al found that 2-(5-nitro-2 H -tetrazol-2-yl)acetamidoxime can serve as a starting compound for the preparation of the corresponding oxadiazoles at room temperature in good yields in both acidic and basic media ( Scheme 40 ) [ 144 ]. The choice of conditions depends on which carboxyl derivative is the second reaction partner.…”

Section: Miscellaneousmentioning

confidence: 99%

Room Temperature Synthesis of Bioactive 1,2,4-Oxadiazoles

Baykov

Shetnev

Semenov

et al. 2023

IJMS

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1,2,4-Oxadiazole is an essential motif in drug discovery represented in many experimental, investigational, and marketed drugs. This review covers synthetic methods that allow the conversion of different types of organic compounds into 1,2,4-oxadiazole at ambient temperature and the practical application of the latter approaches for the preparation of pharmaceutically important molecules. The discussed methods are divided into three groups. The first combines two-stage protocols requiring the preliminary preparation of O-acylamidoximes followed by cyclization under the action of organic bases. The advantages of this route are its swiftness, high efficiency of the cyclization process, and uncomplicated work--up. However, it requires the preparation and isolation of O-acylamidoximes as a separate preliminary step. The second route is a one-pot synthesis of 1,2,4-oxadiazoles directly from amidoximes and various carboxyl derivatives or aldehydes in aprotic bipolar solvents (primarily DMSO) in the presence of inorganic bases. This recently proposed pathway proved to be highly efficient in the field of medicinal chemistry. The third group of methods consists of diverse oxidative cyclizations, and these reactions have found modest application in drug design thus far. It is noteworthy that the reviewed methods allow for obtaining 1,2,4-oxadiazoles with thermosensitive functions and expand the prospects of using the oxadiazole core as an amide- or ester-like linker in the design of bioactive compounds.

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Section: Miscellaneousmentioning

confidence: 99%

Room Temperature Synthesis of Bioactive 1,2,4-Oxadiazoles

Baykov

Shetnev

Semenov

et al. 2023

IJMS

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Rediscovering N‐Methyltetranitropyrrole – A Versatile High Energy Material via Facile Two‐step Eco‐friendly Synthetic Approach

et al. 2022

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A highly efficient 2-step method, where three nitro groups could be directly introduced upon pyrrole moiety in a single step, was developed as an environmentally benign process for the synthesis of N-methyltetranitropyrrole (1) employing metal nitrate/conc. sulphuric acid as the nitrating reagent. This method resulted 1 in high purity having higher thermal stability (273 °C) along with reduced sensitivity (impact sensitivity > 40 J; fricition sensitivity > 360 N), which makes it a versatile high energy material. An over-oxidized new product 1-methyl-3,3,4,4-tetranitropyrrolidine-2,5-dione (4) was also isolated during optimization, whose energetic properties are similar to those of RDX.

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