The first Pummerer cyclizations on solid phase. Convenient construction of oxindoles enabled by a sulfur-link to resin

Laura A. McAllister; Stephen Brand; Remy de Gentile; David J. Procter

doi:10.1039/b307586a

The first Pummerer cyclizations on solid phase. Convenient construction of oxindoles enabled by a sulfur-link to resin

Laura A. McAllister, Stephen Brand, Remy de Gentile, David J. Procter

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

Abstract

a-Sulfanyl-N-aryl-acetamides, attached to resin via the sulfur atom, undergo efficient Pummerer cyclization upon activation of the sulfur link, to give oxindoles, e.g., I. The heterocyclic products can be cleaved from the resin in a traceless manner using samarium(II) iodide. [on SciFinder (R)]

Original language	English
Journal	Chemical Communications
DOIs	https://doi.org/10.1039/b307586a
Publication status	Published - 2003

Keywords

Pummerer reaction; Solid phase synthesis (prepn. of indolones via attachment of N-aryl-a-bromoacetamides to benzyl thiol resin followed by oxidn., Pummerer cyclization, and resin cleavage); Amides Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of indolones via attachment of N-aryl-a-bromoacetamides to benzyl thiol resin followed by oxidn., Pummerer cyclization, and resin cleavage)

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10.1039/b307586a

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title = "The first Pummerer cyclizations on solid phase. Convenient construction of oxindoles enabled by a sulfur-link to resin",

abstract = "a-Sulfanyl-N-aryl-acetamides, attached to resin via the sulfur atom, undergo efficient Pummerer cyclization upon activation of the sulfur link, to give oxindoles, e.g., I. The heterocyclic products can be cleaved from the resin in a traceless manner using samarium(II) iodide. [on SciFinder (R)]",

keywords = "Pummerer reaction; Solid phase synthesis (prepn. of indolones via attachment of N-aryl-a-bromoacetamides to benzyl thiol resin followed by oxidn., Pummerer cyclization, and resin cleavage); Amides Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. of indolones via attachment of N-aryl-a-bromoacetamides to benzyl thiol resin followed by oxidn., Pummerer cyclization, and resin cleavage)",

author = "McAllister, {Laura A.} and Stephen Brand and {de Gentile}, Remy and Procter, {David J.}",

year = "2003",

doi = "10.1039/b307586a",

language = "English",

journal = "Chemical Communications",

issn = "1364-548X",

publisher = "Royal Society of Chemistry",

}

TY - JOUR

T1 - The first Pummerer cyclizations on solid phase. Convenient construction of oxindoles enabled by a sulfur-link to resin

AU - McAllister, Laura A.

AU - Brand, Stephen

AU - de Gentile, Remy

AU - Procter, David J.

PY - 2003

Y1 - 2003

N2 - a-Sulfanyl-N-aryl-acetamides, attached to resin via the sulfur atom, undergo efficient Pummerer cyclization upon activation of the sulfur link, to give oxindoles, e.g., I. The heterocyclic products can be cleaved from the resin in a traceless manner using samarium(II) iodide. [on SciFinder (R)]

AB - a-Sulfanyl-N-aryl-acetamides, attached to resin via the sulfur atom, undergo efficient Pummerer cyclization upon activation of the sulfur link, to give oxindoles, e.g., I. The heterocyclic products can be cleaved from the resin in a traceless manner using samarium(II) iodide. [on SciFinder (R)]

KW - Pummerer reaction; Solid phase synthesis (prepn. of indolones via attachment of N-aryl-a-bromoacetamides to benzyl thiol resin followed by oxidn., Pummerer cyclization, and resin cleavage); Amides Role: RCT (Reactant), RACT (Reactant or reagent) (prepn. o

U2 - 10.1039/b307586a

DO - 10.1039/b307586a

M3 - Article

SN - 1364-548X

JO - Chemical Communications

JF - Chemical Communications

ER -

The first Pummerer cyclizations on solid phase. Convenient construction of oxindoles enabled by a sulfur-link to resin

Abstract

Keywords

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