Syntheses with isoxazoles. Part IV. Ring-opening reactions of 4,5,6,7-tetrahydro-4-oxoisoxazolo[2,3-a]pyridinium salts and related compounds under the influence of tertiary amines
- 1 January 1976
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 11,p. 1241-1244
- https://doi.org/10.1039/p19760001241
Abstract
On treatment of the 4,5,6,7-tetrahydro-4-oxoisoxazolo[2,3-a]pyridinium salts (1) and (3) with triethylamine in methanol, methyl 4-(2-formyl-1-methoxyvinylamino)butyrate (7) and its homologue (9), respectively, are formed. The oxime (13) and the phenylhydrazone (14), under similar conditions, give the methyl piperidin-2-ylideneacetates (16) and (17). The mechanisms of the ring-opening reactions are discussed. Compound (7) is converted spontaneously into N-(trans-3-methoxyacryloyl)-2-pyrrolidone (12), which has been synthesised.Keywords
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