Preparation of Aryl-Susbstituted 2-Oxyindoles by Superelectrophilic Chemistry.
A series of pyridyl-substituted 3-hydroxy-2-oxyindoles have been prepared and reacted with arenes in superacid promoted Friedel-Crafts reactions. The product aryl-substituted 2-oxyindoles are formed in generally good yields. With substituted arenes such as toluene, bromobenzene, or ethyl salicylate, the Friedel-Crafts reactions occur with excellent regioselectivity. A mechanism is proposed involving dicationic, superelectrophilic species leading to the electrophilic aromatic substitution chemistry.
Department of Chemistry and Biochemistry, Northern Illinois University, DeKalb, Illinois 60115, United States, Tel. (815)-753-1959; FAX (815)-753-4802.
Rajasekhar Reddy
RR
Naredla
Erum K
EK
Raja
Douglas A
DA
Klumpp
Friedel-Crafts; Heterocycle; oxyindole; superacid; superelectrophile