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. 2013 Jun 19;54(25):3245-3247.
doi: 10.1016/j.tetlet.2013.04.011.

Preparation of Aryl-Susbstituted 2-Oxyindoles by Superelectrophilic Chemistry

Rajasekhar Reddy Naredla  1 , Erum K Raja, Douglas A Klumpp
Affiliations

Preparation of Aryl-Susbstituted 2-Oxyindoles by Superelectrophilic Chemistry

Rajasekhar Reddy Naredla et al. Tetrahedron Lett. .

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.

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

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Scheme 1
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References

    1. Nicolaou KC, Chen DYK, Huang X, Ling T, Bella M, Snyder SA. J Am Chem Soc. 2004;126:12888–12896. - PubMed
    1. Uddin MK, Reignier SG, Coulter T, Montalbetti C, Graanas C, Butcher S, Krog-Jensen C, Felding J. Bioorg Med Chem Lett. 2007;17:2854–2857. - PubMed
    1. Neel DA, Brown ML, Lander PA, Grese TA, Defauw JM, Doti RA, Fields T, Kelley SA, Smith S, Zimmerman KM, Steinberg MI, Jadhav PK. Bioorg Med Chem Lett. 2005;15:2553–2557. - PubMed
    1. Garrido F, Ibanez J, Gonalons E, Giraldez A. Eur J Med Chem. 1975;10:143–146.
    1. Sarel S, Klug JT, Breaer E, Angel FD. Tetrahedron Lett. 1964:1553.
    2. Flemming I, Loreto MA, Wallace IHM, Michael JP. J Chem Soc Perkin Trans I. 1986:349.
    3. Seno M, Shiraishi S, Suzuki Y, Asahara T. Bull Chem Soc Jpn. 1978;51:1413–1417.
    4. Liu KG, Robichaud AJ. Tetrahedron Lett. 2007;48:461–463.
    5. Barker MW, Sung HS. J Heterocyclic Chem. 1977;14:521–522.
    6. Lee S, Hartwig JF. J Org Chem. 2001;66:3402–3415. - PubMed
    7. Sai KKS, Esteves PM, Tanoue da Penha E, Klumpp DA. J Org Chem. 2008;73:6506–6512. - PubMed
    8. Kumar RS, Rajesh SM, Perumal S, Banerjee D, Yogeeswari P, Sriram D. Eur J Med Chem. 2010;45:411–422. - PubMed
    9. Mai CK, Sammons MF, Sammakia T. Org Lett. 2010;12:2306–2309. - PMC - PubMed
    10. Ahadi S, Moafi L, Feiz A, Bazgir A. Tetrahedron. 2011;67:3954–3958. - PMC - PubMed