Fragmentation of 3-oximino-4-chromanone
Heating either the methanesulfonate ester of 3-oximino-4-chromanone or 3-oximino-4-chromanone and an alternative acylating agent such as p-toluensulfonyl chloride or acetic anhydride in the presence of aqueous base afforded two major fragments: salicyclic acid and 2-carboxyphenoxyacetonitrile. These...
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Published in | Journal of pharmaceutical sciences Vol. 65; no. 3; p. 397 |
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Main Authors | , |
Format | Journal Article |
Language | English |
Published |
United States
01.03.1976
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Subjects | |
Online Access | Get more information |
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Summary: | Heating either the methanesulfonate ester of 3-oximino-4-chromanone or 3-oximino-4-chromanone and an alternative acylating agent such as p-toluensulfonyl chloride or acetic anhydride in the presence of aqueous base afforded two major fragments: salicyclic acid and 2-carboxyphenoxyacetonitrile. These compounds are derived from two separate cleavage pathways involving the acylated oxime. In one pathway, fragmentation appears to be assisted by the ether ring oxygen; in the other, it is assisted by the alpha-carbonyl group of the oxime ester. |
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ISSN: | 0022-3549 |
DOI: | 10.1002/jps.2600650320 |