A novel and efficient synthesis of 3-fluorooxindoles from indoles mediated by Selectfluor.
[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.
Takeuchi
Y
Y
Faculty of Pharmaceutical Sciences, Toyama Medical & Pharmaceutical University, Japan. takeuchi@ms.toyama-mpu.ac.jp
Tarui
T
T
Shibata
N
N
D003979:Diazonium Compounds; D005461:Fluorine / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*
D003979:Diazonium Compounds; D007211:Indoles; D005461:Fluorine; C408750:selectfluor