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.
| Original language | English (US) |
|---|---|
| Pages (from-to) | 3245-3247 |
| Number of pages | 3 |
| Journal | Tetrahedron Letters |
| Volume | 54 |
| Issue number | 25 |
| DOIs | |
| State | Published - Jun 19 2013 |
| Externally published | Yes |
Bibliographical note
Funding Information:We gratefully acknowledge the support of the NIH-National Institute of General Medical Sciences ( GM085736-01A1 ) and the Northern Illinois University for Great Journeys Fellowship (R.R.N.).
Keywords
- Friedel-Crafts
- Heterocycle
- Oxyindole
- Superacid
- Superelectrophile
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