Novel ring contraction of 3-hydroxy-2,4(1H,3H)-quinolinediones in aqueous alkali. The first convenient route to 2-hydroxyindoxyls
Language English Country United States Media print
Document type Journal Article, Research Support, Non-U.S. Gov't
PubMed
11559192
DOI
10.1021/jo015786d
PII: jo015786d
Knihovny.cz E-resources
- MeSH
- Alkalies chemistry MeSH
- Biological Factors chemical synthesis MeSH
- Quinolines chemical synthesis MeSH
- Indoles chemical synthesis MeSH
- Water chemistry MeSH
- Publication type
- Journal Article MeSH
- Research Support, Non-U.S. Gov't MeSH
- Names of Substances
- Alkalies MeSH
- Biological Factors MeSH
- Quinolines MeSH
- Indoles MeSH
- indoxyl MeSH Browser
- Water MeSH
Ring contraction of 3-hydroxy-2,4(1H,3H)-quinolinediones (1) in aqueous potassium hydroxide resulted in the formation of 2-hydroxyindoxyls and/or dioxindoles. The choice of N-substituent and the reaction conditions govern the chemoselectivity of the reaction. N-Phenyl-substituted derivatives 1 give 2-hydroxyindoxyls, while N-alkyl- and N-benzyl-substituted derivatives afford the corresponding dioxindols. On the basis of byproduct analysis, as well as independent experiments, the most plausible reaction mechanism is proposed.
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