Literature DB >> 10814398

A novel and efficient synthesis of 3-fluorooxindoles from indoles mediated by Selectfluor.

Y Takeuchi1, T Tarui, N Shibata.   

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.

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Year:  2000        PMID: 10814398     DOI: 10.1021/ol991400y

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  3 in total

1.  Synthetic Studies of 3-(3-Fluorooxindol-3-yl)-l-alanine.

Authors:  Tomoya Fujiwara; Bin Yin; Meixiang Jin; Kenneth L Kirk; Yoshio Takeuchi
Journal:  J Fluor Chem       Date:  2008       Impact factor: 2.050

2.  Synthesis of Fluorinated 3,6-Dihydropyridines and 2-(Fluoromethyl)pyridines by Electrophilic Fluorination of 1,2-Dihydropyridines with Selectfluor®.

Authors:  Nadiia V Pikun; Arkadij Sobolev; Aiva Plotniece; Martins Rucins; Brigita Vigante; Marina Petrova; Ruslan Muhamadejev; Karlis Pajuste; Yuriy G Shermolovich
Journal:  Molecules       Date:  2020-07-09       Impact factor: 4.411

3.  Green oxidation of indoles using halide catalysis.

Authors:  Jun Xu; Lixin Liang; Haohao Zheng; Yonggui Robin Chi; Rongbiao Tong
Journal:  Nat Commun       Date:  2019-10-18       Impact factor: 14.919

  3 in total

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