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== Triazole ==
{{short description|Class of heterocyclic compounds}}
{{chembox
| verifiedrevid = 477239870
| ImageFile = Triazole-isomers.png
| ImageSize = 250px
| ImageAlt = Structural formulae of 1,2,3-triazole and 1,2,4-triazole
| IUPACName = Triazole
| OtherNames = Azole
}}


Triazole is a five-membered heterocyclic compound containing three nitrogen atoms and two carbon atoms. It is classified as an azole compound and is widely used in various fields, including pharmaceuticals, agriculture, and materials science. Triazoles exhibit diverse chemical and biological properties, making them valuable building blocks in the synthesis of numerous compounds.
'''Triazole''' is a class of [[heterocyclic compound]]s containing a five-membered ring of two [[carbon]] atoms and three [[nitrogen]] atoms. The molecular formula of triazoles is C_H_N_. Triazoles are divided into two isomers: 1,2,3-triazole and 1,2,4-triazole, which differ in the position of the nitrogen atoms in the ring.


=== History ===
==Structure and properties==
Triazoles are aromatic compounds, and they exhibit significant stability due to the delocalization of electrons across the ring. The two isomers, 1,2,3-triazole and 1,2,4-triazole, have distinct properties and reactivity due to the different arrangement of nitrogen atoms.


The discovery of triazoles dates back to the late 19th century when German chemist Ludwig Knorr first synthesized 1,2,4-triazole in 1883. Since then, several other triazole derivatives have been developed and studied for their unique properties and applications.
===1,2,3-Triazole===
1,2,3-Triazole is a planar, aromatic compound that is often synthesized through the [[Huisgen azide-alkyne cycloaddition]], a reaction that forms a five-membered ring by the 1,3-dipolar cycloaddition of an [[azide]] and an [[alkyne]]. This reaction can be catalyzed by [[copper]] (CuAAC) or [[ruthenium]] (RuAAC) to improve selectivity and yield.


=== Structure and Properties ===
[[File:Huisgen-azide-alkyne-cycloaddition.png|thumb|center|400px|Huisgen azide-alkyne cycloaddition]]


Triazoles possess a planar structure with three nitrogen atoms and two carbon atoms arranged in a ring. The nitrogen atoms in the triazole ring can act as electron donors, making triazoles highly reactive and versatile in chemical reactions. The presence of multiple nitrogen atoms also contributes to their biological activity.
[[File:CuAAC-triazole-synthesis.png|thumb|center|400px|Copper-catalyzed azide-alkyne cycloaddition (CuAAC)]]


Triazoles exhibit a range of physical and chemical properties depending on their substituents and functional groups. They are generally stable compounds with good solubility in organic solvents. The melting and boiling points of triazoles vary depending on their specific structures.
[[File:RuAAC-triazole-synthesis.png|thumb|center|400px|Ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC)]]


=== Applications ===
===1,2,4-Triazole===
1,2,4-Triazole is another isomer of triazole, which also exhibits aromaticity. It is commonly used in the synthesis of various pharmaceuticals and agrochemicals due to its versatile chemical properties.


==== Pharmaceuticals ====
==Applications==
Triazoles are widely used in the pharmaceutical industry as they form the core structure of many [[antifungal]] agents, such as [[fluconazole]] and [[itraconazole]]. They are also used in the synthesis of [[herbicides]], [[insecticides]], and [[plant growth regulators]].


Triazoles have gained significant attention in the pharmaceutical industry due to their diverse biological activities. Many triazole-based drugs have been developed for the treatment of various diseases, including antifungal, antiviral, and anticancer agents. For example, fluconazole and voriconazole are widely used antifungal drugs that belong to the triazole class.
==Synthesis==
 
The synthesis of triazoles can be achieved through various methods, with the Huisgen azide-alkyne cycloaddition being one of the most prominent. This reaction can be catalyzed by copper or ruthenium to form 1,2,3-triazoles selectively.
==== Agriculture ====
 
Triazole compounds also find applications in agriculture as plant growth regulators and fungicides. They help enhance crop yield, improve plant resistance to diseases, and control fungal infections. Triazole-based fungicides, such as tebuconazole and propiconazole, are commonly used to protect crops from fungal pathogens.
 
==== Materials Science ====
 
In materials science, triazoles are utilized as building blocks for the synthesis of functional materials. They can be incorporated into polymers, coatings, and composites to impart specific properties, such as improved mechanical strength, thermal stability, and electrical conductivity. Triazole-based materials have found applications in areas such as electronics, aerospace, and energy storage.
 
=== Safety and Environmental Considerations ===
 
Triazoles are generally considered safe when used in accordance with recommended guidelines. However, like any chemical compound, they should be handled with care to avoid potential hazards. Some triazole derivatives may exhibit toxicity or environmental persistence, requiring proper disposal and handling practices.
 
=== See Also ===


==Related pages==
* [[Azole]]
* [[Azole]]
* [[Heterocyclic compound]]
* [[Heterocyclic compound]]
* [[Antifungal drugs]]
* [[Cycloaddition]]
* [[Fungicides]]
 
=== References ===


<references />
==References==
{{reflist}}


[[Category:Chemical compounds]]
[[Category:Heterocyclic compounds]]
[[Category:Heterocyclic compounds]]
[[Category:Pharmaceuticals]]
[[Category:Triazoles]]
[[Category:Agricultural chemicals]]
[[Category:Materials science]]

Revision as of 23:58, 9 February 2025

Class of heterocyclic compounds


Chemical Compound
Identifiers
CAS Number
PubChem CID
ChemSpider ID
UNII
ChEBI
ChEMBL
Properties
Chemical Formula
Molar Mass
Appearance
Density
Melting Point
Boiling Point
Hazards
GHS Pictograms [[File:|50px]]
GHS Signal Word
GHS Hazard Statements
NFPA 704 [[File:|50px]]
References

Triazole is a class of heterocyclic compounds containing a five-membered ring of two carbon atoms and three nitrogen atoms. The molecular formula of triazoles is C_H_N_. Triazoles are divided into two isomers: 1,2,3-triazole and 1,2,4-triazole, which differ in the position of the nitrogen atoms in the ring.

Structure and properties

Triazoles are aromatic compounds, and they exhibit significant stability due to the delocalization of electrons across the ring. The two isomers, 1,2,3-triazole and 1,2,4-triazole, have distinct properties and reactivity due to the different arrangement of nitrogen atoms.

1,2,3-Triazole

1,2,3-Triazole is a planar, aromatic compound that is often synthesized through the Huisgen azide-alkyne cycloaddition, a reaction that forms a five-membered ring by the 1,3-dipolar cycloaddition of an azide and an alkyne. This reaction can be catalyzed by copper (CuAAC) or ruthenium (RuAAC) to improve selectivity and yield.

Huisgen azide-alkyne cycloaddition
Copper-catalyzed azide-alkyne cycloaddition (CuAAC)
Ruthenium-catalyzed azide-alkyne cycloaddition (RuAAC)

1,2,4-Triazole

1,2,4-Triazole is another isomer of triazole, which also exhibits aromaticity. It is commonly used in the synthesis of various pharmaceuticals and agrochemicals due to its versatile chemical properties.

Applications

Triazoles are widely used in the pharmaceutical industry as they form the core structure of many antifungal agents, such as fluconazole and itraconazole. They are also used in the synthesis of herbicides, insecticides, and plant growth regulators.

Synthesis

The synthesis of triazoles can be achieved through various methods, with the Huisgen azide-alkyne cycloaddition being one of the most prominent. This reaction can be catalyzed by copper or ruthenium to form 1,2,3-triazoles selectively.

Related pages

References

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