Syntheses with isoxazoles. Part III. Rearrangement of 4,5,6,7-tetrahydro-4-hydroxyiminoisoxazolo[2,3-a]pyridinium salts into derivatives of pyrrolo[3,2-b]pyridin-2-one
- 1 January 1974
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- p. 158-160
- https://doi.org/10.1039/p19740000158
Abstract
When 4,5,6,7-tetrahydro-4-hydroxyiminoisoxazolo[2,3-a]pyridinium chloride (5) or bromide (6) was heated with acetic anhydride, rearrangement to the corresponding 4-acetyl-7-halogeno-5,6-dihydro-4H-pyrrolo[3,2-b]-pyridin-2(1H)-one (9) or (8) occurred. The bromo-derivative (8) was hydrogenated to give a debrominated dihydro-derivative (10), and hydrolysed to the deacetylated derivative (11). Mechanisms for the rearrangement are suggested.Keywords
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