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- Title
A Facile Synthesis of 2-Oxazolines via Dehydrative Cyclization Promoted by Triflic Acid.
- Authors
Yang, Tao; Huang, Chengjie; Jia, Jingyang; Wu, Fan; Ni, Feng
- Abstract
2-oxazolines are common moieties in numerous natural products, pharmaceuticals, and functional copolymers. Current methods for synthesizing 2-oxazolines mainly rely on stoichiometric dehydration agents or catalytic dehydration promoted by specific catalysts. These conditions either generate stoichiometric amounts of waste or require forcing azeotropic reflux conditions. As such, a practical and robust method that promotes dehydrative cyclization while generating no byproducts would be attractive to oxazoline production. Herein, we report a triflic acid (TfOH)-promoted dehydrative cyclization of N-(2-hydroxyethyl)amides for synthesizing 2-oxazolines. This reaction tolerates various functional groups and generates water as the only byproduct. This method affords oxazoline with inversion of α-hydroxyl stereochemistry, suggesting that alcohol is activated as a leaving group under these conditions. Furthermore, the one-pot synthesis protocol of 2-oxazolines directly from carboxylic acids and amino alcohols is also provided.
- Subjects
RING formation (Chemistry); CATALYSTS; AMINO alcohols; STEREOCHEMISTRY; NATURAL products; CARBOXYLIC acids; OXAZOLINE
- Publication
Molecules, 2022, Vol 27, Issue 24, p9042
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules27249042