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
Current Organic Chemistry
Title: The Witkop-Winterfeldt-Oxidation of Indoles
Volume: 11 Issue: 2
Author(s): Matthias Mentel and Rolf Breinbauer
Affiliation:
Keywords: ozone, corynanthyrin, tetrahydroharman alkaloids, Peroxyacids, Autoxidation, singlett oxygen
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.
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Cite this article as:
Mentel Matthias and Breinbauer Rolf, The Witkop-Winterfeldt-Oxidation of Indoles, Current Organic Chemistry 2007; 11 (2) . https://dx.doi.org/10.2174/138527207779316426
DOI https://dx.doi.org/10.2174/138527207779316426 |
Print ISSN 1385-2728 |
Publisher Name Bentham Science Publisher |
Online ISSN 1875-5348 |
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