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Preparation of Aryl-Susbstituted 2-Oxyindoles by Superelectrophilic Chemistry.

ABSTRACT: 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.

SUBMITTER: Naredla RR

PROVIDER: S-EPMC3775391 | biostudies-literature | 2013 Jun

REPOSITORIES: biostudies-literature

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Preparation of Aryl-Susbstituted 2-Oxyindoles by Superelectrophilic Chemistry.

Naredla Rajasekhar Reddy RR Raja Erum K EK Klumpp Douglas A DA

Tetrahedron letters 20130601 25

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 chemist ...[more]

PMID: 24058216

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