K2CO3-Mediated Intramolecular Oxa-Michael Cyclization of α,β-Unsaturated Ketoximes: Synthesis of Densely Arene-Substituted 2-Isoxazolines Bearing a Quaternary Center

Ram Singh Jat; Raveendrababu Kothapalli; M. Bhanuchandra

doi:10.1055/a-2242-6435

Synthesis, Inhaltsverzeichnis

Synthesis 2024; 56(10): 1593-1600
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

Ram Singh Jat

^aDepartment of Chemistry, School of Chemical Sciences and Pharmacy, Central University of Rajasthan, Bandarsindri, Rajasthan-305817, India

,

Raveendrababu Kothapalli

^bSCIM Govt. College, Tanuku, West Godavari (Dist.), Andhra Pradesh-534211, India

,

M. Bhanuchandra∗

^aDepartment of Chemistry, School of Chemical Sciences and Pharmacy, Central University of Rajasthan, Bandarsindri, Rajasthan-305817, India

› Institutsangaben

Abstract

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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 reaction

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