Ylide mediated carbonyl homologations for the preparation of isatin derivatives

Ylide mediated carbonyl homologations for the preparation of isatin derivatives

An exceptionally mild method for the preparation of isatin derivatives has been developed using a sulfur ylide mediated carbonyl homologation sequence starting from anthranilic acid precursors. This method proceeds at ambient temperature via a sulfur ylide intermediate without the need for protectio...

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Veröffentlicht in:Organic & biomolecular chemistry 2014-01, Vol.12 (3), p.406-409
Hauptverfasser: Lollar, Christina T, Krenek, Katherine M, Bruemmer, Kevin J, Lippert, Alexander R
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Sprache:eng
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Isatin - chemical synthesis
Isatin - chemistry
Molecular Structure
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container_title Organic & biomolecular chemistry
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creator Lollar, Christina T
Krenek, Katherine M
Bruemmer, Kevin J
Lippert, Alexander R
description An exceptionally mild method for the preparation of isatin derivatives has been developed using a sulfur ylide mediated carbonyl homologation sequence starting from anthranilic acid precursors. This method proceeds at ambient temperature via a sulfur ylide intermediate without the need for protection of the amine or chromatographic isolation of the intermediate ylide. Gentle oxidation of the sulfur ylides provides isatin derivatives with N-H, N-alkyl, N-aryl substitution, electron-rich and electron-poor aromatic rings, and heterocyclic aromatic systems. We anticipate that this method will greatly expand the accessibility of complex isatin derivatives.
doi_str_mv 10.1039/c3ob42024h
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source MEDLINE; Royal Society Of Chemistry Journals 2008-; Alma/SFX Local Collection
subjects Isatin - chemical synthesis
Isatin - chemistry
Molecular Structure
title Ylide mediated carbonyl homologations for the preparation of isatin derivatives
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