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.

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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
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article

Synthesis of 1,3‐Oxazole‐Substituted 2‐Naphthols and Phenols From Their Corresponding Ethers via Claisen Rearrangement

Chintakunta Ramesh, Sujeet Kumar
Advanced Synthesis & Catalysis
Synthesis of heterocyclic compounds
article

Synthesis of 1,3‐Oxazole‐Substituted 2‐Naphthols and Phenols From Their Corresponding Ethers via Claisen Rearrangement

Chintakunta Ramesh, Sujeet Kumar
article en

Abstract

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.

Advanced Synthesis & CatalysisVol. 368(5)
Central Drug Research Institute (IN), Academy of Scientific and Innovative Research (IN)
Openalex Percentile: Top 49%
Synthesis of heterocyclic compounds
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