1,3,4-Oxadiazole is a nitrogen and oxygen containing

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

, and one of the four isomers of

oxadiazole Oxadiazoles are a class of heterocyclic aromatic chemical compound of the azole family; with the molecular formula C2H2N2O. There are four isomers of oxadiazole: File:1,2,3-oxadiazole.svg, 1,2,3-oxadiazole File:1,2,4-oxadiazole.svg, 1,2,4-oxadiazo ...

Derivatives

1,3,4-Oxadiazole itself is not commonly used in organic chemistry, but many of its

derivatives The derivative of a function is the rate of change of the function's output relative to its input value. Derivative may also refer to: In mathematics and economics * Brzozowski derivative in the theory of formal languages * Formal derivative, an ...

are important. For example,

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 ...

is an

HIV The human immunodeficiency viruses (HIV) are two species of ''Lentivirus'' (a subgroup of retrovirus) that infect humans. Over time, they cause acquired immunodeficiency syndrome (AIDS), a condition in which progressive failure of the immune ...

drug which contains an 1,3,4-oxadiazole ring. Other pharmaceutical drugs containing the 1,3,4-oxadiazole ring include

fenadiazole Fenadiazole (), also known as phénadiazole () and sold under the brand names Hypnazol, Eudormil, and Viodor, is a hypnotic and sedative medication which has been used to treat insomnia but is no longer marketed. It is described as a non-barbitura ...

zibotentan Zibotentan (INN; development code ZD4054) is an experimental anti-cancer drug candidate in development by AstraZeneca. It is an endothelin receptor antagonist. Zibotentan was granted fast track status for the treatment of prostate cancer by the ...

, and

tiodazosin Tiodazosin is an α1-adrenergic receptor antagonist. See also * Terazosin Terazosin, sold under the brand name Hytrin among others, is a medication used to treat symptoms of an enlarged prostate and high blood pressure. For high blood press ...

. 1,3,4-Oxadiazole derivatives can be synthesized in a variety of ways. One pathway is from oxidation of

tetrazole Tetrazoles are a class of synthetic organic heterocyclic compound, consisting of a 5-member ring of four nitrogen atoms and one carbon atom. The name tetrazole also refers to the parent compound with formula CH2N4, of which three isomers can be f ...

s in the presence of

aldehyde In organic chemistry, an aldehyde () is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred to as an aldehyde but can also be classified as a formyl grou ...

s. Similarly, the reaction of tetrazoles with

acyl chloride In organic chemistry, an acyl chloride (or acid chloride) is an organic compound with the functional group . Their formula is usually written , where R is a side chain. They are reactive derivatives of carboxylic acids (). A specific example o ...

s provides oxadiazoles. Both methods involve the release of N₂.

References

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