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This research demonstrates synthesis of oxazole-substituted compounds in a methodology that suggests efficient uses of ionic liquids.
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.
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Kumar et al. (2026) studied this question.