Preparation of 3-Alkyl-Oxindoles by Copper(II)-Mediated C-H, Ar-H Coupling Followed by Decarboxyalkylation

David S. Pugh; Johannes E. M. N. Klein; Alexis Perry; Richard J. K. Taylor

doi:10.1055/s-0029-1219392

Preparation of 3-Alkyl-Oxindoles by Copper(II)-Mediated C-H, Ar-H Coupling Followed by Decarboxyalkylation

David S. Pugh, Johannes E. M. N. Klein, Alexis Perry, Richard J. K. Taylor

Chemistry

Research output: Contribution to journal › Article › peer-review

Abstract

A novel route for the conversion of anilides into 3-alkyloxindoles is described in which a copper(II)-mediated cyclization process is followed by an acid-mediated decarboxyalkylation. Scope and limitation studies are reported together with a telescoped variant which incorporates in situ N-deprotection.

Original language	English
Pages (from-to)	934-938
Number of pages	5
Journal	Synlett
Issue number	6
DOIs	https://doi.org/10.1055/s-0029-1219392
Publication status	Published - Apr 2010

Keywords

oxindoles
3-alkyl-oxindoles
anilides
cyclisation
copper(II) catalysis
C-H activation
decarboxyalkylation
OXINDOLES
HYDROXYLATION
LACTAMS
ENOLATE

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10.1055/s-0029-1219392

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title = "Preparation of 3-Alkyl-Oxindoles by Copper(II)-Mediated C-H, Ar-H Coupling Followed by Decarboxyalkylation",

abstract = "A novel route for the conversion of anilides into 3-alkyloxindoles is described in which a copper(II)-mediated cyclization process is followed by an acid-mediated decarboxyalkylation. Scope and limitation studies are reported together with a telescoped variant which incorporates in situ N-deprotection.",

keywords = "oxindoles, 3-alkyl-oxindoles, anilides, cyclisation, copper(II) catalysis, C-H activation, decarboxyalkylation, OXINDOLES, HYDROXYLATION, LACTAMS, ENOLATE",

author = "Pugh, {David S.} and Klein, {Johannes E. M. N.} and Alexis Perry and Taylor, {Richard J. K.}",

year = "2010",

month = apr,

doi = "10.1055/s-0029-1219392",

language = "English",

pages = "934--938",

journal = "Synlett",

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T1 - Preparation of 3-Alkyl-Oxindoles by Copper(II)-Mediated C-H, Ar-H Coupling Followed by Decarboxyalkylation

AU - Pugh, David S.

AU - Klein, Johannes E. M. N.

AU - Perry, Alexis

AU - Taylor, Richard J. K.

PY - 2010/4

Y1 - 2010/4

N2 - A novel route for the conversion of anilides into 3-alkyloxindoles is described in which a copper(II)-mediated cyclization process is followed by an acid-mediated decarboxyalkylation. Scope and limitation studies are reported together with a telescoped variant which incorporates in situ N-deprotection.

AB - A novel route for the conversion of anilides into 3-alkyloxindoles is described in which a copper(II)-mediated cyclization process is followed by an acid-mediated decarboxyalkylation. Scope and limitation studies are reported together with a telescoped variant which incorporates in situ N-deprotection.

KW - oxindoles

KW - 3-alkyl-oxindoles

KW - anilides

KW - cyclisation

KW - copper(II) catalysis

KW - C-H activation

KW - decarboxyalkylation

KW - OXINDOLES

KW - HYDROXYLATION

KW - LACTAMS

KW - ENOLATE

UR - http://www.scopus.com/inward/record.url?scp=77949892812&partnerID=8YFLogxK

U2 - 10.1055/s-0029-1219392

DO - 10.1055/s-0029-1219392

M3 - Article

SN - 1437-2096

SP - 934

EP - 938

JO - Synlett

JF - Synlett

IS - 6

ER -

Preparation of 3-Alkyl-Oxindoles by Copper(II)-Mediated C-H, Ar-H Coupling Followed by Decarboxyalkylation

Abstract

Keywords

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