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.
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| http://www.ncbi.nlm.nih.gov/pmc/articles/PMC3775391 | PMC |
| http://dx.doi.org/10.1016/j.tetlet.2013.04.011 | DOI Listing |
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