Allenes. Part 42. Nucleophilic addition of hydroxylamine to allenic and acetylenic nitriles; synthesis of 3-alkyl-5-amino, 5-amino-3-phenyl-, and 3-amino-5-phenyl-isoxazoles
- 1 January 1984
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 1079-1083
- https://doi.org/10.1039/p19840001079
Abstract
Hydroxylamine adds to allenic nitriles to give 3-alkyl-5-aminoisoxazoles in excellent yield. Hydroxyacetylenic nitriles similarly give 5-amino-3-(1-hydroxyalkyl)isoxazoles. Phenylpropynenitrile under varying conditions of temperature and solvent yields mainly 5-amino-3-phenylisoxazole with varying amounts of 3-amino-5-phenylisoxazole as a by-product.Keywords
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