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Synlett
DOI: 10.1055/a-2744-2024
Letter
Published as part of the Special Issue dedicated to Prof. S. Chandrasekaran on his 80th birthday

HFIP-Promoted Intramolecular Oximation of O-Propargyl Hydroxylamines for the Synthesis of 2-Isoxazolines

Autoren

  • Santosh J. Gharpure 

    1   Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, India (Ringgold ID: RIN29491)

  • Sandesh Balu Bhujbal

    1   Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, India (Ringgold ID: RIN29491)

  • Shipra Somani

    1   Department of Chemistry, Indian Institute of Technology Bombay, Mumbai, India (Ringgold ID: RIN29491)

We thank ANRF for funding (CRG/2023/001183).
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Graphical Abstract

Dedication

Dedicated to Prof. S. Chandrasekaran: New Synthetic Methods and Strategies in Organic Synthesis.

Abstract

A concise and efficient intramolecular oximation enables the rapid and streamlined synthesis of 2-isoxazolines. This metal-free approach offers a broad substrate scope under mild reaction conditions. The successful demonstration of gram-scale and one-pot synthesis highlights both the versatility and scalability of the method. The synthetic utility of this method is further exemplified by converting 2-isoxazolines into β-hydroxy ketones. This method was further used for the synthesis of firefly luciferase inhibitors.

Keywords

Intramolecular oximation - HFIP - O-Propargyl hydroxylamine - Isoxazoline - One-pot synthesis - Luciferase inhibitors

Supplementary Material



Publikationsverlauf

Eingereicht: 17. September 2025

Angenommen nach Revision: 11. November 2025

Accepted Manuscript online:
11. November 2025

Artikel online veröffentlicht:
05. Dezember 2025

© 2025. Thieme. All rights reserved.

Georg Thieme Verlag KG
Oswald-Hesse-Straße 50, 70469 Stuttgart, Germany

 

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