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A novel and efficient synthesis of 3-fluorooxindoles from indoles mediated by Selectfluor
Y Takeuchi1, T Tarui, N Shibata
1Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University, Japan. takeuchi@ms.toyama-mpu.ac.jp
Organic Letters
|May 18, 2000
Abstract:
[reaction: see text] Treatment of several 3-substituted indoles, including derivatives of tryptophan and serotonin, with commercially available Selectfluor in acetonitrile/water furnished 3-substituted 3-fluorooxindoles in good to high yields. Since 3-fluorooxindoles obtained are sterically similar to both oxindoles and 3-hydroxyoxindoles, they should be useful as probes for investigating the enzymatic mechanism of indole biosynthesis and metabolism.