# [3 + 2] Cycloadditions of Tertiary Amine N‑Oxides and Azoarenes as a Route to Substituted 1,2,4-Triazolidines

**Authors:** Nicholas A. Frankos, Malavika S. Nair, Aiden M. Lane, Megan M. Glista, Joshua K. Graber, Abbigail E. F. Black, Trista G. L. X. Newman, Elias R. Griffin, Kiera M. Luca, Eric J. Chartier, David B. Heisler, Thomas D. Montgomery

PMC · DOI: 10.1021/acsorginorgau.5c00098 · ACS Organic & Inorganic Au · 2025-12-05

## TL;DR

A new method to synthesize triazolidines using amine N-oxides and azoarenes, with high yields and potential antibacterial properties.

## Contribution

A base-mediated [3 + 2] cycloaddition method for synthesizing substituted 1,2,4-triazolidines with high yields.

## Key findings

- 29 novel triazolidines were synthesized with yields up to 99%.
- Density functional theory calculations provided insights into the reaction mechanism.
- Preliminary data showed antibacterial properties of the synthesized compounds.

## Abstract

We have developed a synthesis of 29 novel 1,2,4-triazolidines
using
tertiary amine N-oxides and a wide range of substituted
azoarenes. Our method utilizes a base-mediated [3 + 2] cycloaddition,
starting from either commercially available or easily accessible precursors
to generate triazolidines in yields up to 99%. Density functional
theory calculations were performed in parallel to the experimental
work to provide insights into the reactivity patterns and the overall
mechanism. Finally, preliminary biological data are included on the
antibacterial properties of these compounds.

## Full-text entities

- **Chemicals:** 1,2,4-Triazolidines (-)

## Full text

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## Figures

6 figures with captions in the complete paper: https://tomesphere.com/paper/PMC12879182/full.md

## References

97 references — full list in the complete paper: https://tomesphere.com/paper/PMC12879182/full.md

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Source: https://tomesphere.com/paper/PMC12879182