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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 Lindell
A 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.

History

Publication status

  • Published

Journal

Synlett

ISSN

0936-5214

Publisher

Thieme Medical Publishers

Issue

3

Volume

2006

Page range

463-465

Department affiliated with

  • Chemistry Publications

Full text available

  • No

Peer reviewed?

  • Yes

Legacy Posted Date

2012-02-06

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