Preparation of aryl-substituted 2-oxyindoles by superelectrophilic chemistry

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

doi:10.1016/j.tetlet.2013.04.011

Preparation of aryl-substituted 2-oxyindoles by superelectrophilic chemistry

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

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12 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 language	English (US)
Pages (from-to)	3245-3247
Number of pages	3
Journal	Tetrahedron Letters
Volume	54
Issue number	25
DOIs	https://doi.org/10.1016/j.tetlet.2013.04.011
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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title = "Preparation of aryl-substituted 2-oxyindoles by superelectrophilic chemistry",

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",

author = "Naredla, {Rajasekhar Reddy} and Raja, {Erum K.} and Klumpp, {Douglas A.}",

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.). ",

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AU - Naredla, Rajasekhar Reddy

AU - Raja, Erum K.

AU - Klumpp, Douglas A.

N1 - 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.).

PY - 2013/6/19

Y1 - 2013/6/19

N2 - 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.

AB - 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.

KW - Friedel-Crafts

KW - Heterocycle

KW - Oxyindole

KW - Superacid

KW - Superelectrophile

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Preparation of aryl-substituted 2-oxyindoles by superelectrophilic chemistry

Abstract

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Keywords

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