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Synthesis 2024; 56(10): 1593-1600
DOI: 10.1055/a-2242-6435
DOI: 10.1055/a-2242-6435
paper
K2CO3-Mediated Intramolecular Oxa-Michael Cyclization of α,β-Unsaturated Ketoximes: Synthesis of Densely Arene-Substituted 2-Isoxazolines Bearing a Quaternary Center
We gratefully acknowledge the Department of Science and Technology - Science and Engineering Research Board (DST-SERB) (EEQ/2022/000490) for research funding. We also thank Central the University of Rajasthan for support. R.S.J. thanks Council of Scientific & Industrial Research (CSIR), India for the award of a Senior Research Fellowship (CSIR-SRF).
Abstract
An efficient K2CO3-mediated intramolecular oxa-Michael cyclization of β,β-diarylated α,β-unsaturated ketoximes is described. This methodology allows access to arene-rich 2-isoxazoline derivatives bearing a quaternary center in excellent yields with an operationally simple experimental procedure. Deuterium-scrambling experiments were carried out to shed light on the reaction pathway. To demonstrate the synthetic utility of the method, a large-scale synthesis and Ullmann-type C–N bond-formation reaction between pyrazole and dibrominated isoxazoline was performed.
Key words
2-isoxazolines - α,β-unsaturated ketoximes - oxa-Michael cyclization - Ullmann-type amination - base-mediated reactionSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/a-2242-6435.
- Supporting Information
Publication History
Received: 12 December 2023
Accepted after revision: 10 January 2024
Accepted Manuscript online:
10 January 2024
Article published online:
13 February 2024
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