- Source: Pfitzinger reaction
The Pfitzinger reaction (also known as the Pfitzinger-Borsche reaction) is the chemical reaction of isatin with base and a carbonyl compound to yield substituted quinoline-4-carboxylic acids.
Several reviews have been published.
Reaction mechanism
The reaction of isatin with a base such as potassium hydroxide hydrolyses the amide bond to give the keto-acid 2. This intermediate can be isolated, but is typically not. A ketone (or aldehyde) will react with the aniline to give the imine (3) and the enamine (4). The enamine will cyclize and dehydrate to give the desired quinoline (5).
Variations
= Halberkann variant
=Reaction of N-acyl isatins with base gives 2-hydroxy-quinoline-4-carboxylic acids.
See also
Camps quinoline synthesis
Friedländer synthesis
Niementowski quinazoline synthesis
Doebner reaction
Talnetant, Cinchocaine
References
Kata Kunci Pencarian:
- Pfitzinger reaction
- Pfitzinger
- Doebner reaction
- List of organic reactions
- Bicinchoninic acid assay
- Quinoline
- 1-Tetralone
- Friedländer synthesis
- Isatin
- Diazonium compound
