Synthesis of functionalized 2-oxindoles by Friedel–Crafts reactions. Issue 33 (12th August 2015)

• Record Type: Journal Article
• Authors: Gasonoo, Makafui; Klumpp, Douglas A.
• Is Part Of: Tetrahedron letters. Volume 56:Issue 33(2015)
• Page Start: 4737
• Page End: 4739
• Publication Date: 2015-08-12
• Subjects: 2-Oxyindole -- Friedel–Crafts -- Superacid -- Heterocycles -- Carbocation; Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1016/j.tetlet.2015.06.028
• Languages: English
• ISSNs: 0040-4039

Abstract

Graphical abstract: Abstract: 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.