Pfitzinger reaction
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| Pfitzinger reaction | |||||||||||||
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| Named after | Wilhelm Pfitzinger | ||||||||||||
| Reaction type | ring-condensation | ||||||||||||
| Reaction | |||||||||||||
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| Conditions | |||||||||||||
| Typical solvents | protic | ||||||||||||
| Identifiers | |||||||||||||
| RSC ontology ID | RXNO:0000109 | ||||||||||||
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.[1][2]
Several reviews have been published.[3][4][5]
Reaction mechanism
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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
[edit | edit source]Halberkann variant
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Reaction of N-acyl isatins with base gives 2-hydroxy-quinoline-4-carboxylic acids.[6]
See also
[edit | edit source]- Camps quinoline synthesis
- Friedländer synthesis
- Niementowski quinazoline synthesis
- Doebner reaction
- Talnetant, Cinchocaine
References
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