Oxadiazoles are a class of

heterocyclic A heterocyclic compound or ring structure is a cyclic compound that has atoms of at least two different elements as members of its ring(s). Heterocyclic chemistry is the branch of organic chemistry dealing with the synthesis, properties, and ...

aromatic In chemistry, aromaticity is a chemical property of cyclic ( ring-shaped), ''typically'' planar (flat) molecular structures with pi bonds in resonance (those containing delocalized electrons) that gives increased stability compared to satur ...

chemical compound of the

azole Azoles are a class of five-membered heterocyclic compounds containing a nitrogen atom and at least one other non-carbon atom (i.e. nitrogen, sulfur, or oxygen) as part of the ring. Their names originate from the Hantzsch–Widman nomenclature. Th ...

family; with the molecular formula C₂H₂N₂O. There are four

isomer In chemistry, isomers are molecules or polyatomic ions with identical molecular formulae – that is, same number of atoms of each element – but distinct arrangements of atoms in space. Isomerism is existence or possibility of isomers. Iso ...

s of oxadiazole: File:1,2,3-oxadiazole.svg, 1,2,3-oxadiazole File:1,2,4-oxadiazole.svg, 1,2,4-oxadiazole File:1,2,5-oxadiazole.svg, 1,2,5-oxadiazole
(furazan) File:1,3,4-oxadiazole.svg, 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 Raltegravir, sold under the brand name Isentress, is an antiretroviral medication used, together with other medication, to treat HIV/AIDS. It may also be used, as part of post exposure prophylaxis, to prevent HIV infection following potential ex ...

butalamine Butalamine is a vasodilator. Synthesis Check with imolamine (alternate nitrogen reacts) The halogenation of benzamidoxime 32-90-1 22-31-1(1) with chlorine and subsequent reaction with cyanamide Cyanamide is an organic compound with the f ...

fasiplon Fasiplon (RU 33203) is a nonbenzodiazepine anxiolytic drug from the imidazopyrimidine family of drugs. Fasiplon binds strongly to benzodiazepine sites on the GABAA receptor and has similar anxiolytic effects in animals, but with less sedative ...

oxolamine Oxolamine is a cough suppressant that is available as a generic drug in many jurisdictions. Oxolamine also has anti-inflammatory activity, which causes a reduction in irritation of the nerve receptors of the respiratory tract. It is mainly u ...

, and

pleconaril Pleconaril (Picovir) is an antiviral drug that was being developed by Schering-Plough for prevention of asthma exacerbations and common cold symptoms in patients exposed to picornavirus respiratory infections. Pleconaril, administered either or ...

. The 1,2,3-isomer is unstable and ring-opens to form the

diazo The diazo group is an organic moiety consisting of two linked nitrogen atoms ( azo) at the terminal position. Overall charge neutral organic compounds containing the diazo group bound to a carbon atom are called diazo compounds or diazoalkanes ...

ketone In organic chemistry, a ketone is a functional group with the structure R–C(=O)–R', where R and R' can be a variety of carbon-containing substituents. Ketones contain a carbonyl group –C(=O)– (which contains a carbon-oxygen double bo ...

tautomer Tautomers () are structural isomers (constitutional isomers) of chemical compounds that readily interconvert. The chemical reaction interconverting the two is called tautomerization. This conversion commonly results from the relocation of a hydr ...

; however, it does exist within the unusual

sydnone Sydnones are mesoionic heterocyclic chemical compounds possessing a 1,2,3-oxadiazole core with a keto group in the 5 position. Like other mesoionic compounds they are di-polar, possessing both positive and negative charges which are delocalized ...

motif. In 2018, a compound called bis(1,2,4-oxadiazole)bis(methylene) dinitrate which might have a 1.5 times the power of

TNT Trinitrotoluene (), more commonly known as TNT, more specifically 2,4,6-trinitrotoluene, and by its preferred IUPAC name 2-methyl-1,3,5-trinitrobenzene, is a chemical compound with the formula C6H2(NO2)3CH3. TNT is occasionally used as a reagen ...

was developed at the

United States Army Research Laboratory The U.S. Army Combat Capabilities Development Command Army Research Laboratory (DEVCOM ARL) is the U.S. Army's foundational research laboratory. ARL is headquartered at the Adelphi Laboratory Center (ALC) in Adelphi, Maryland. Its largest singl ...

(ARL) working with the

Los Alamos National Laboratory Los Alamos National Laboratory (often shortened as Los Alamos and LANL) is one of the sixteen research and development laboratories of the United States Department of Energy (DOE), located a short distance northwest of Santa Fe, New Mexico, ...

References

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