Triazole

A triazole (Htrz) refers to any of the heterocyclic compounds with molecular formula C₂H₃N₃, having a five-membered ring of two carbon atoms and three nitrogen atoms. There are two sets of isomers that differ in the relative positions of the three nitrogen atoms. Each of these has two tautomers that differ by which nitrogen has a hydrogen bonded to it:

1H-1,2,3-Triazole

1H-1,2,3-Triazole

2H-1,2,3-Triazole

2H-1,2,3-Triazole

1H-1,2,4-Triazole

1H-1,2,4-Triazole

4H-1,2,4-Triazole

4H-1,2,4-Triazole

Derivatives

The triazole antifungal drugs include fluconazole, isavuconazole, itraconazole, voriconazole, pramiconazole, ravuconazole, and posaconazole.

The triazole plant protection fungicides include epoxiconazole, triadimenol, propiconazole, prothioconazole, metconazole, cyproconazole, tebuconazole, flusilazole and paclobutrazol.

Benzotriazole is used in chemical photography as a restrainer and fog-suppressant.

Importance in agriculture

1,2,4-Triazole

1,2,4-Triazole is one of a pair of isomeric chemical compounds with molecular formula C₂H₃N₃, called triazoles, which have a five-membered ring of two carbon atoms and three nitrogen atoms. 1,2,4-Triazole is a basic aromatic heterocycle. 1,2,4-Triazole derivatives find use in a wide variety of applications, most notably as antifungals such as fluconazole and itraconazole.

1,2,4-Triazoles can be prepared using the Einhorn–Brunner reaction or the Pellizzari reaction.

The ring structure appears in certain N-heterocyclic carbenes.

See also

References

1,2,3-Triazole

1,2,3-Triazole is one of a pair of isomeric chemical compounds with molecular formula C₂H₃N₃, called triazoles, which have a five-membered ring of two carbon atoms and three nitrogen atoms. 1,2,3-Triazole is a basic aromatic heterocycle.

Substituted 1,2,3-triazoles can be produced using the azide alkyne Huisgen cycloaddition in which an azide and an alkyne undergo a 1,3-dipolar cycloaddition reaction.

It is a surprisingly stable structure compared to other organic compounds with three adjacent nitrogen atoms. However, flash vacuum pyrolysis at 500 °C leads to loss of molecular nitrogen (N₂) to produce aziridine. Certain triazoles are relatively easy to cleave due to so-called ring-chain tautomerism. One manifestation is found in the Dimroth rearrangement.

1,2,3-Triazole finds use in research as a building block for more complex chemical compounds, including pharmaceutical drugs such as tazobactam.

References