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 elements as members of its ring(s). Heterocyclic organic chemistry is the branch of organic chemistry dealing with the synthesis, proper ...
, and one of the four isomers of
oxadiazole.
Derivatives
1,3,4-Oxadiazole itself is not commonly used in organic chemistry, but many of its
derivatives 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 e ...
is an
HIV drug which contains an 1,3,4-oxadiazole ring. Other pharmaceutical drugs containing the 1,3,4-oxadiazole ring include
fenadiazole,
zibotentan, and
tiodazosin.
1,3,4-Oxadiazole derivatives can be synthesized in a variety of ways.
One pathway is from oxidation of
tetrazole
A tetrazole is a chemical synthesis, 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 - a whitish crystalline powder with the f ...
s in the presence of
aldehyde
In organic chemistry, an aldehyde () (lat. ''al''cohol ''dehyd''rogenatum, dehydrogenated alcohol) is an organic compound containing a functional group with the structure . The functional group itself (without the "R" side chain) can be referred ...
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 N
2.
See also
*
Furazan (1,2,5-oxadiazole)
References
{{DEFAULTSORT:Oxadiazole, 1, 3, 4-
Oxadiazoles