Synthesis of 5-Aminooxazoles and Zwitterionic Fused Imidazolones by I <sub>2</sub> -Mediated C–H Amination
Iodine-mediated C-H amination reactions of β-ketoamides with alkylamines have been developed under transition-metal-free conditions. In the presence of Na<sub>2</sub>CO<sub>3</sub> as the base, I<sub>2</sub>-promoted annulation of β-ketoamides with benzylamines produces 5-aminooxazole derivatives. Replacement of arylmethylamines with tetrahydroisoquinolines leads to the formation of novel zwitterionic fused imidazolone products. The synthetic protocols are operationally simple and can be conveniently conducted on a gram scale.
Authors
- Junbiao Chang (ORCID: https://orcid.org/0000-0001-6236-1256)
- Qing-an Xiong
- Wenquan Yu (ORCID: https://orcid.org/0000-0002-3711-0006)
- Yanliang Liu
- Manman Wang (ORCID: https://orcid.org/0000-0002-1801-6321)
- Zhigang Yin (ORCID: https://orcid.org/0000-0001-9566-9417)
- Pu Wang (ORCID: https://orcid.org/0000-0002-7555-0512)
Institutions
- Zhengzhou University of Light Industry (CN)
- Zhengzhou University (CN)
- Standard Bio (Norway) (NO)
- Material (Belgium) (BE)
- Shanghai Industrial Technology Institute (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-11-07
- DOI
- https://doi.org/10.1021/acs.orglett.5c04066
- Citations
- 1
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 0.94