Synthesis of 1,3‐Oxazole‐Substituted 2‐Naphthols and Phenols From Their Corresponding Ethers via Claisen Rearrangement
We report the synthesis of 1,3‐oxazole‐substituted 2‐naphthols and phenols from aryl heterobenzyl ethers via Claisen rearrangement by employing a Lewis acid‐based ionic liquid as a promoter. Heterobenzyl‐2‐naphthyl ethers bearing electron‐donating and ‐withdrawing groups produced exclusively [3,3]‐sigmatropic Claisen rearranged products in excellent yields under the standard reaction conditions. Meanwhile, aryl heterobenzyl ethers bearing electron‐donating and ‐withdrawing groups produced a mixture of rearranged products via [1,3] or [3,3]‐Claisen or para ‐Claisen rearrangement. We also demonstrated a gram‐scale reaction for this methodology. The reported ionic liquid can be reused for the subsequent cycles.
Authors
- Chintakunta Ramesh (ORCID: https://orcid.org/0000-0001-7327-4430)
- Sujeet Kumar
Institutions
- Central Drug Research Institute (IN)
- Academy of Scientific and Innovative Research (IN)
Publication Details
- Journal
- Advanced Synthesis & Catalysis
- Published
- 2026-02-17
- DOI
- https://doi.org/10.1002/adsc.70295
- Primary Topic
- Synthesis of heterocyclic compounds
- Type
- article
- Field-Weighted Citation Impact
- 0.00