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The Preparation of 2-Isoxazolines from O-Propargylic Hydroxylamines via a Tandem Rearrangement-Cyclisation Reaction
| Content Provider | Scilit |
|---|---|
| Author | Lindell, Stephen Pennicott, Lewis |
| Copyright Year | 2006 |
| Description | A method for the conversion of O-propargylic hydroxylÂamines 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 $K_{2}CO_{3}$. 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. |
| Related Links | http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-2006-926232.pdf |
| Ending Page | 0465 |
| Page Count | 3 |
| Starting Page | 0463 |
| ISSN | 09365214 |
| e-ISSN | 14372096 |
| DOI | 10.1055/s-2006-926232 |
| Journal | Synlett |
| Issue Number | 03 |
| Volume Number | 2006 |
| Language | English |
| Publisher | Georg Thieme Verlag KG |
| Publisher Date | 2006-02-06 |
| Access Restriction | Open |
| Subject Keyword | Journal: Synlett Organic Chemistry Isoxazoline Synthesis O-propargylic Hydroxylamine Sigmatropic Rearrangement |
| Content Type | Text |
| Resource Type | Article |
| Subject | Organic Chemistry |
