139286-77-4Relevant academic research and scientific papers
New rearrangement of 4-isoxazoline system: Conversion of ketones into α,β-unsaturated amides
Chiacchio, Ugo,Rescifina, Antonio,Chiacchio, Maria Assunta,Romeo, Giovanni,Romeo, Roberto
, p. 3718 - 3720 (2007/10/03)
A new rearrangement pattern of the 4-isoxazoline system is reported. The reaction, starting from 3,3-disubstituted derivatives and leading to α,β-unsaturated amides, proceeds through the quaternarization of the nitrogen atom and involves the heterolytic cleavage of C3-N bond, assisted by the formation of a relatively stable intermediate. The overall process represents a useful conversion of ketones into α,β-unsaturated amides.
Novel Approach to the Ring-Opening of 4-Isoxazolines: One-Pot Synthesis of α,β-Enones
Chiacchio, Ugo,Liguori, Angelo,Rescifina, Antonio,Romeo, Giovanni,Rossano, Flavia,et al.
, p. 123 - 132 (2007/10/02)
Treatment of 4-isoxazoline derivatives with methyl iodide affords α,β-enones in excellent yields.The novel rearrangement pathway, through an intermediate isoxazolinium salt, is interpretable on the basis of the base removal of the hydrogen atom at N-CH3 group.
