Home Chemistry Heterocyclic Building Blocks Triazoles 2H-1,2,3-Triazole
Cycloaddition reactions: 2H-1,2,3-triazole is known for its reactivity in cycloaddition reactions, particularly with alkynes or other electron-deficient compounds. The most famous reaction involving 2H-1,2,3-triazole is the Huisgen 1,3-dipolar cycloaddition, commonly referred to as the "click chemistry" reaction, which involves the reaction of an azide and an alkyne to form a triazole ring.
Nucleophilic substitution reactions: 2H-1,2,3-triazole can participate in nucleophilic substitution reactions at its nitrogen atoms. For example, it can be alkylated or acylated at the nitrogen positions using suitable electrophiles.
Metal-catalyzed reactions: Transition metal-catalyzed reactions can be performed with 2H-1,2,3-triazole. For instance, copper-catalyzed azide-alkyne cycloaddition (CuAAC) reactions are commonly used in bioconjugation and click chemistry.
Reduction reactions: 2H-1,2,3-triazoles can undergo reduction reactions to form the corresponding hydrazides or amines. This can be achieved using reducing agents like sodium borohydride (NaBH4) or hydrogen gas (H2) in the presence of a suitable catalyst.
Oxidation reactions: Depending on the conditions, 2H-1,2,3-triazoles can be oxidized to form various products, including N-oxides or other functionalized derivatives.
Ring-opening reactions: In some cases, 2H-1,2,3-triazole can undergo ring-opening reactions under specific conditions, leading to the formation of different compounds.
Substitution reactions: The carbon atoms in the triazole ring can undergo various substitution reactions, particularly when the appropriate functional groups are present.
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