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

Synthesis DOI: 10.1055/a-2242-6435 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. [...] Georg Thieme Verlag KG Rüdigerstraße 14, 70469 Stuttgart, GermanyArticle in Thieme eJournals: Table of contents  |  Abstract  |  Full text

Source: Synthesis - February 13, 2024 Category: Chemistry Authors: Jat, Ram Singh Kothapalli, Raveendrababu Bhanuchandra, M. Tags: paper Source Type: research