Synthesis of functionalized 2-oxindoles by Friedel–Crafts reactions

Synthesis of functionalized 2-oxindoles by Friedel–Crafts reactions

[Display omitted] A series of acetonyl-substituted 3-hydroxy-2-oxindoles have been prepared and reacted with arenes in superacid promoted Friedel–Crafts reactions. The product aryl-substituted 2-oxindoles are formed in generally good yields. With substituted arenes such as toluene, bromobenzene, or...

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Bibliographic Details
Published in:Tetrahedron letters Vol. 56; no. 33; pp. 4737 - 4739
Main Authors: Gasonoo, Makafui, Klumpp, Douglas A.
Format: Journal Article
Language:English
Published: Elsevier Ltd 12-08-2015
Subjects:
2-Oxyindole
Carbocation
Friedel–Crafts
Heterocycles
Superacid
Friedel–Crafts
Superacid
Carbocation
Heterocycles
2-Oxyindole
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Summary:[Display omitted] A series of acetonyl-substituted 3-hydroxy-2-oxindoles have been prepared and reacted with arenes in superacid promoted Friedel–Crafts reactions. The product aryl-substituted 2-oxindoles are formed in generally good yields. With substituted arenes such as toluene, bromobenzene, or anisole, the Friedel–Crafts reactions occur with excellent regioselectivity. A mechanism is proposed involving carbocationic electrophiles leading to the aromatic substitution chemistry.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2015.06.028