Iron(III)-Catalyzed Methanesulfonic-Acid-Mediated [3 + 2 + 1C] Annulation of Enaminones with 1,3-Dioxolane: Access to 2-Hydroxy-1,2-dihydropyridines
An iron(III)-catalyzed methanesulfonic-acid-mediated [3 + 2 + 1C] annulation of enaminones assembling a 1,2-dihydropyridine (1,2-DHP) scaffold has been developed for the first time. This approach facilitates the rapid synthesis of 2-hydroxy-1,2-DHP derivatives in moderate to excellent yields with a broad substrate scope under mild conditions. The employment of 1,3-dioxolane as both a 1C synthon and solvent enables simultaneous incorporation of both a carbon atom and a hydroxy group into 1,2-DHPs. Application potential of this protocol is proven by its gram-scale preparation and further derivatizations.
Authors
- Yu Xu (ORCID: https://orcid.org/0000-0001-6898-4307)
- Fuchao Yu (ORCID: https://orcid.org/0000-0001-5557-3824)
- Shaolin Yang (ORCID: https://orcid.org/0000-0001-6946-0556)
- Yuanzheng Wei
- Yu Zhang (ORCID: https://orcid.org/0009-0005-7730-8817)
- Huimin Hu (ORCID: https://orcid.org/0000-0001-5712-3624)
- Menglin Peng
- Junliang Wang (ORCID: https://orcid.org/0000-0002-8078-8090)
- Xiaohong Wang (ORCID: https://orcid.org/0000-0001-8925-5736)
Institutions
- Kunming University of Science and Technology (CN)
- Yunnan University (CN)
- Yunnan University of Traditional Chinese Medicine (CN)
Publication Details
- Journal
- Organic Letters
- Published
- 2025-09-04
- DOI
- https://doi.org/10.1021/acs.orglett.5c03165
- Citations
- 3
- Primary Topic
- Catalytic C–H Functionalization Methods
- Type
- article
- Field-Weighted Citation Impact
- 2.81
Funders
- National Natural Science Foundation of China
- Natural Science Foundation of Yunnan Province