The preparation of 2-isoxazolines from O-propargylic hydroxylamines via a tandem rearrangement-cyclisation reaction

Pennicott, Lewis and Lindell, Stephen (2006) The preparation of 2-isoxazolines from O-propargylic hydroxylamines via a tandem rearrangement-cyclisation reaction. Synlett, 2006 (3). pp. 463-465. ISSN 0936-5214

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Abstract

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.

Item Type: Article
Schools and Departments: School of Life Sciences > Chemistry
Depositing User: Lewis Pennicott
Date Deposited: 06 Feb 2012 20:39
Last Modified: 21 Jul 2015 06:54
URI: http://sro.sussex.ac.uk/id/eprint/27240
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