Preparation of aryl-substituted 2-oxyindoles by superelectrophilic chemistry

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

Research output: Contribution to journalArticlepeer-review

9 Scopus citations

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 languageEnglish (US)
Pages (from-to)3245-3247
Number of pages3
JournalTetrahedron Letters
Volume54
Issue number25
DOIs
StatePublished - Jun 19 2013

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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