Ring Expansion Strategy toward Seven/Eight-Membered 1,4-Diazaheterocycle Ketones from Imidazolidines with Cyclobutenones/Diarylcyclopropenones
A ring expansion strategy for the synthesis of diverse homopiperazin-5-ones and 1,4-diazocine-5-ones is described. Imidazolidines undergo Zn(OTf)<sub>2</sub>-catalyzed ring expansion with cyclobutenones to produce homopiperazin-5-one derivatives. Alternatively, Cu(MeCN)<sub>4</sub>BF<sub>4</sub>-catalyzed (5 + 3) cycloaddition between imidazolidines and diarylcyclopropenones provides access to eight-membered 1,4-diazocine-5-ones under mild conditions.
Authors
- Jiangtao Sun (ORCID: https://orcid.org/0000-0003-2516-3466)
- Shengbiao Tang (ORCID: https://orcid.org/0000-0003-4860-5458)
- Ying Shao (ORCID: https://orcid.org/0000-0002-7379-8266)
- Yulu Zhang (ORCID: https://orcid.org/0000-0002-5551-3597)
- Wen Shao (ORCID: https://orcid.org/0000-0002-5427-079X)
- Dongmei Cai
Institutions
- Institute of Catalysis and Petrochemistry (RU)
- Changzhou University (CN)
- Xiangtan University (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-08-20
- DOI
- https://doi.org/10.1021/acs.orglett.5c02626
- Citations
- 1
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.94
Funders
- National Natural Science Foundation of China