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Current Organic Chemistry

Editor-in-Chief

ISSN (Print): 1385-2728
ISSN (Online): 1875-5348

The Witkop-Winterfeldt-Oxidation of Indoles

Author(s): Matthias Mentel and Rolf Breinbauer

Volume 11, Issue 2, 2007

Page: [159 - 176] Pages: 18

DOI: 10.2174/138527207779316426

Price: $65

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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