Journal
SYNLETT
Volume 28, Issue 2, Pages 260-264Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1588335
Keywords
lactams; lactones; indoles; heterocycles; cycloadditions
Categories
Funding
- NSF [RUI: 1362813]
- Hobart College
- William Smith College
- Drs. Carey and Cohen Family
- Dave and Brenda Rickey Family
- Dr. Edward Franks Family
- Patchett Family
- Division Of Chemistry
- Direct For Mathematical & Physical Scien [1362183] Funding Source: National Science Foundation
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The electrophilic substitution of indoles with tetronic acid and N-acetyltetramic acid mediated by BF3OEt2 was investigated. This strategy allowed for the preparation of nine indole-substituted furan-2-ones (indolyl--lactones) and 3-pyrrolin-2-ones (indolyl--lactams) and is more straightforward than previously reported synthetic methods. During the course of our investigation, we also discovered a facile synthesis of tetronates and a tetramate via a BF3-mediated addition of alcohols to tetronic acid and N-acetyltetramic acid, respectively.
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