AlCl<sub>3</sub>-mediated “Heine-type” ring-opening of <i>N</i>-cyclopropylamides for the synthesis of 5-methyl-2-oxazolines
A ring-opening rearrangement reaction of <i>N</i>-cyclopropylamides is shown to occur in the presence of AlCl<sub>3</sub>. The mechanism proposed herein involves the "Heine-type" aziridine intermediate and C-Cl or C-O bond formation. This protocol provides quick access to <i>N</i>-(2-chloropropyl)amides and 5-methyl-2-oxazolines using simple and readily available starting materials.
Authors
- Congcong Wan
- Xiang Zhang (ORCID: https://orcid.org/0000-0002-3513-5226)
- Hongling Wang (ORCID: https://orcid.org/0000-0002-5092-0476)
Institutions
- North West Agriculture and Forestry University (CN)
- Northwest A&F University (CN)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob01040c
- Primary Topic
- Cyclopropane Reaction Mechanisms
- Type
- article
- Field-Weighted Citation Impact
- 0.00