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
Related Journals
Current Bioactive Compounds
Current Organic Synthesis
Mini-Reviews in Organic Chemistry
Current Organic Synthesis
Mini-Reviews in Organic Chemistry
Letters in Organic Chemistry
Mini-Reviews in Organic Chemistry
Letters in Organic Chemistry
The Natural Products Journal
Letters in Organic Chemistry
The Natural Products Journal
Current Catalysis
The Natural Products Journal
Current Catalysis
Current Organocatalysis
Current Catalysis
Current Organocatalysis
Current Microwave Chemistry
Current Organocatalysis
Current Microwave Chemistry
Current Bioactive Compounds
Current Microwave Chemistry
Current Bioactive Compounds
Current Organic Synthesis
Related Books
2-Deoxy-D-Glucose: Chemistry and Biology
Chiral Ionic Liquids: Applications in Chemistry and Technology
Basics of Organic Chemistry: A Textbook for Undergraduate Students
Chiral Ionic Liquids: Applications in Chemistry and Technology
Basics of Organic Chemistry: A Textbook for Undergraduate Students
Advances in Organic Synthesis
Basics of Organic Chemistry: A Textbook for Undergraduate Students
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
The Synthetic Methods, Structures, and Properties of the Ca-C σ Bond Organocalcium Containing Compounds
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Chemistry of Bipyrazoles: Synthesis and Applications
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
Advanced Nanocatalysis for Organic Synthesis and Electroanalysis
Advances in Organic Synthesis
2-Deoxy-D-Glucose: Chemistry and Biology
Advances in Organic Synthesis
2-Deoxy-D-Glucose: Chemistry and Biology
Chiral Ionic Liquids: Applications in Chemistry and Technology
31