Mild, efficient, and solvent-free synthesis of 4-hydroxy-2-quinolinones
[Display omitted] •Anilines are converted to malonic acid monoanilides by reacting with Meldrum’s acid.•Malonic acid monoanilides are converted to 4-hydroxy-2-quinolinones by MSAA.•Malonic acid monoanilides are prone to decarboxylation above 70 °C.•The reactions require mild conditions (70 °C or low...
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Veröffentlicht in: | Tetrahedron letters 2020-04, Vol.61 (16), p.151778, Article 151778 |
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Sprache: | eng |
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Zusammenfassung: | [Display omitted]
•Anilines are converted to malonic acid monoanilides by reacting with Meldrum’s acid.•Malonic acid monoanilides are converted to 4-hydroxy-2-quinolinones by MSAA.•Malonic acid monoanilides are prone to decarboxylation above 70 °C.•The reactions require mild conditions (70 °C or lower).
Malonic acid monoanilides were obtained in excellent yield from the reaction of anilines with Meldrum’s acid under solvent-free conditions. The malonic acid monoanilide intermediates were then treated with methanesulfonic acid anhydride (MSAA) to produce 4-hydroxy-2-quinolinones in excellent yield. It should be noted that both reactions had to be run under mild conditions to avoid the decarboxylation of the malonic acid monoanilide intermediate. |
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ISSN: | 0040-4039 1873-3581 |
DOI: | 10.1016/j.tetlet.2020.151778 |