[3 + 2] Cycloadditions of Tertiary Amine <i>N</i> -Oxides and Azoarenes as a Route to Substituted 1,2,4-Triazolidines
We have developed a synthesis of 29 novel 1,2,4-triazolidines using tertiary amine <i>N</i>-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.
Authors
- David B. Heisler (ORCID: https://orcid.org/0000-0002-6482-4215)
- Thomas D. Montgomery (ORCID: https://orcid.org/0000-0002-6526-8564)
- Aiden M. Lane (ORCID: https://orcid.org/0000-0003-2959-5434)
- Eric J. Chartier (ORCID: https://orcid.org/0009-0002-1548-3642)
- M. Sivasankaran Nair (ORCID: https://orcid.org/0009-0007-2142-6472)
- Taysa-Ja Newman (ORCID: https://orcid.org/0009-0006-8510-8150)
- Ann E. Black (ORCID: https://orcid.org/0009-0005-4790-3578)
- Elias D. Griffin (ORCID: https://orcid.org/0009-0005-2890-5201)
- Nicholas A. Frankos (ORCID: https://orcid.org/0009-0003-9926-7177)
- Joshua K. Graber (ORCID: https://orcid.org/0009-0000-5021-3598)
- Megan M. Glista (ORCID: https://orcid.org/0009-0005-6550-9347)
- Kiera M. Luca (ORCID: https://orcid.org/0009-0001-0016-3788)
Institutions
- Duquesne University (US)
Publication Details
- Journal
- ACS Organic & Inorganic Au
- Published
- 2025-12-05
- DOI
- https://doi.org/10.1021/acsorginorgau.5c00098
- Primary Topic
- Click Chemistry and Applications
- Type
- article
- Field-Weighted Citation Impact
- 0.00