Triazole: Synthesis, Structure & Derivatives

Instructor: Korry Barnes

Korry has a Ph.D. in organic chemistry and teaches college chemistry courses.

The focus of this lesson will be on a class of organic compounds known as triazoles. The specific aspects of triazoles to be discussed include their general structure, their synthesis, and a few derivatives that are important in terms of their application.

There's a Fungus Among Us

What's the first thing that comes to mind when you hear the word fungus? Most people probably don't think happy thoughts when it comes to fungi at all. Things like fungal infections and diseases most likely come to mind. When a fungal infection strikes or farmers need to protect their crops from fungi, there's a certain class of organic compounds that actually do a pretty good job of fighting those pesky little bugs. They're called triazoles. Organic compounds (compounds that are carbon and hydrogen-based) that contain the triazole functional group tend to be the go-to candidates to help combat various fungi in the clinical setting and in agricultural applications.

In this lesson, we are going to get an introduction to triazoles. Our main topics that we will explore are the general structure of triazoles, how they are made in terms of their synthesis, and finally some important derivatives of triazoles that are important as drug compounds and also as agricultural pesticides. Let's get started, and see what triazoles can do for us!

Structure of Triazoles

It will probably help to start with a good definition of what a triazole is. Triazoles are heterocyclic compounds that contain five atoms within the ring structure and have the general formula C2 H3 N3. The word ''heterocyclic'' seems complicated, but the prefix hetero- simply means it contains atoms other than carbon inside the ring, and cyclic means it's a ring structure.

Triazoles can exist in one of two isomers (same chemical formula but different atom connectivity), with the two forms simply being different from one another by the placement of the nitrogen and carbon atoms within the ring. The two isomers are called either 1,2,3-triazole or 1,2,4-triazole. The 1,2,3 isomer has all three nitrogen atoms adjacent to one another, while the 1,2,4 isomer has two nitrogens adjacent to each other, and the other nitrogen is sandwiched between two carbon atoms.

Structurers of the two triazole isomers

Synthesis of Triazoles

Now that we have a good idea of the general structure of triazoles, let's talk about a couple of ways they can be made in the laboratory. We will be breaking down the synthesis based on the two isomers, the 1,2,3- and 1,2,4-triazole cases.

1,2,3-Triazole Synthesis

In terms of making the 1,2,3-triazole isomer, by far the most popular and commonly utilized method is what's known as the Huisgen Azide-Alkyne method. The great thing about this reaction is we only need two simple building blocks, an azide and an alkyne, to make our triazole. An azide is an organic compound that has three nitrogen atoms bonded to a general R group, and an alkyne is any organic compound that has a carbon-carbon triple bond. When we take the two starting materials and react them together, a 1,2,3-triazole is formed as the sole product.

1,2,3-Triazole synthesis from an organic azide and an alkyne

1,2,4-Triazole Synthesis

If we want to make the 1,2,4-triazole isomer, a great way to do this is by reacting an organic hydrazine with formamide and then microwave it. Just in case you were wondering, sometimes organic reactions (a lot like popcorn) are run in a microwave! An organic hydrazine contains a generic R group bonded to two nitrogen atoms, and formamide is a building block that contains a carbonyl group (carbon-oxygen double bond) connected to a nitrogen atom and a hydrogen.

1,2,4-Triazole synthesis from an organic hydrazine and formamide

Triazole Derivatives

As we mentioned previously, organic compounds that contain the triazole functional group are particularly useful in helping combat fungal infections and also find application in agricultural systems as pesticides. Fluconazole is a triazole that is used to help treat a variety of fungal infections in humans. It is commonly used to help prevent candidiasis (a type of yeast infection) in people who are at high risk for infection like after an organ transplant or for babies who have a low birth weight.

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