What type of study is this?

This is a QM(DFT-D3) Calculations study (also classified as: Observational).

September 5, 2025Open Access

Reactivity of 2H-Azirines in Copper-Catalyzed Azide–Alkyne Cycloaddition Reactions

LJLukáš JaneckýCharles University AMAndrea MadabeniUniversity of Padua EJEliška JelínkováCzech Academy of Sciences, Institute of Organic Chemistry and Biochemistry

Key Points

C–C bond formation at position five of the 1,2,3-triazole was observed, correcting previous misidentifications.
Employing calibrated quantum mechanical (QM(DFT-D3)) calculations fully explained the reaction mechanism involved in this process.
Functionalization of primary products yielded various substituted compounds, including pyrimidine and furan.
The findings may enable novel synthetic routes in organic chemistry by revealing new pathways for complex molecule synthesis.

Abstract

A reaction between azide, alkyne and 2H-azirine resulted in C–C bond formation at position five of 1,2,3-triazole, instead of previously misidentified C–N bond connectivity. The reaction mechanism of this C–C bond formation on the triazole ring was fully explained by employing calibrated QM(DFT-D3) calculations. Functionalization of primary products provided substituted pyrimidine, furan or 1,3-oxazepine.

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