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The preparation of 2-isoxazolines from O-propargylic hydroxylamines via a tandem rearrangement-cyclisation reaction
journal contribution
posted on 2023-06-08, 07:11 authored by Lewis Pennicott, Stephen LindellA method for the conversion of O-propargylic hydroxylamines into 2-isoxazolines in 60-84% yield is described. For 3-alkylpropargyl or 3-arylpropargyl hydroxylamines this was achieved by heating a methanolic solution of the hydrochloride salt in the presence of K2CO3. In the case of the 3-unsubstituted compounds, the hydrochloride salts were first converted to the free bases, which rearranged upon heating in methanol. In one case, the methodology was extended to enable the direct transformation of a O-propargyl phthalimide into a 2-isoxazoline in 65% yield by treatment with methyl hydrazine at room temperature over 19 hours.
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Publication status
- Published
Journal
SynlettISSN
0936-5214Publisher
Thieme Medical PublishersExternal DOI
Issue
3Volume
2006Page range
463-465Department affiliated with
- Chemistry Publications
Full text available
- No
Peer reviewed?
- Yes
Legacy Posted Date
2012-02-06Usage metrics
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