The Witkop-Winterfeldt-Oxidation of Indoles

Author(s): Matthias Mentel, Rolf Breinbauer.

Journal Name: Current Organic Chemistry

Volume 11 , Issue 2 , 2007

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Abstract:

In the early 1950s Witkop described in a series of papers that oxidation of indoles with a variety of oxidation reagents leads to the formation of quinolones. The mechanism of this reaction involves the oxidative cleavage of the 2,3- double bond of the indole moiety (Witkop-oxidation) followed by a Camps-cyclization forming the quinolone ring. Winterfeldt identified conditions which allow a one pot Witkop-oxidation/Camps-cyclization sequence and applied this strategy for the synthesis of pyrrolo[2,3-c]quinolones starting from 1,2,3,4-tetrahydro-β-carbolines. This review gives a comprehensive description of all described examples of this reaction including a definition of scope and limitations and a discussion of the mechanism of this transformation.

Keywords: ozone, corynanthyrin, tetrahydroharman alkaloids, Peroxyacids, Autoxidation, singlett oxygen

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Article Details

VOLUME: 11
ISSUE: 2
Year: 2007
Page: [159 - 176]
Pages: 18
DOI: 10.2174/138527207779316426
Price: $58

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