Literature DB >> 24058216

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

Rajasekhar Reddy Naredla1, Erum K Raja, Douglas A Klumpp.   

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.

Entities:  

Keywords:  Friedel-Crafts; Heterocycle; oxyindole; superacid; superelectrophile

Year:  2013        PMID： 24058216      PMCID： PMC3775391          DOI： 10.1016/j.tetlet.2013.04.011

Source DB:  PubMed          Journal:  Tetrahedron Lett        ISSN： 0040-4039            Impact factor:   2.415


  11 in total

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