Oxadiazoles are a class of heterocyclic aromatic chemical compounds of the azole family with the molecular formula C2H2N2O. There are four isomers of oxadiazole:
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1,2,3-oxadiazole
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1,2,4-oxadiazole
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1,2,5-oxadiazole
(furazan) -
1,3,4-oxadiazole
1,2,4-Oxadiazole, 1,2,5-oxadiazole, and 1,3,4-oxadiazole are all known and appear in a variety of pharmaceutical drugs including raltegravir, butalamine, fasiplon, oxolamine, and pleconaril. The 1,2,3-isomer is unstable and ring-opens to form the diazoketone tautomer; however, it does exist within the unusual sydnone motif.
In 2018, a compound called bis(1,2,4-oxadiazole)bis(methylene) dinitrate which might have 1.5 times the power of TNT was developed at the United States Army Research Laboratory (ARL) working with the Los Alamos National Laboratory.
References
- ^ John A. Joule; Keith Mills (28 May 2013). Heterocyclic Chemistry. John Wiley & Sons. p. 569. ISBN 1-118-68164-9.
- Nguyen, Minh Tho; Hegarty, Anthony F.; Elguero, José (August 1985). "Can 1,2,3‐Oxadiazole be Stable?". Angewandte Chemie International Edition in English. 24 (8): 713–715. doi:10.1002/anie.198507131.
- "Double oxadiazole could replace TNT". Chemical & Engineering News. 5 June 2018.
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