Pfitzinger reaction
You don't need to be Editor-In-Chief to add or edit content to WikiDoc. You can begin to add to or edit text on this WikiDoc page by clicking on the edit button at the top of this page. Next enter or edit the information that you would like to appear here. Once you are done editing, scroll down and click the Save page button at the bottom of the page.
The Pfitzinger reaction (also known as the Pfitzinger-Borsche reaction) is the chemical reaction of isatin with base and a carbonyl compound to give substituted quinoline-4-carboxylic acids.[1][2]
Several reviews have been published.[3][4][5]
Contents |
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 quiniline (5).
Variations
Halberkann variant
Reaction of N-acyl isatins with base gives 2-hydroxy-quinoline-4-carboxylic acids.[6]
References
- ↑ Pfitzinger, W. J. Prakt. Chem. 1886, 33, 100.
- ↑ Pfitzinger, W. J. Prakt. Chem. 1888, 38, 582.
- ↑ Manske, R. H. Chem. Rev. 1942, 30, 126. (Review)
- ↑ Bergstrom, F. W. Chem. Rev. 1944, 35, 152. (Review)
- ↑ Shvekhgeimer, M. G.-A. Chemistry of Heterocyclic Compounds 2004, 40, 257-294. (Review, doi:10.1023/B:COHC.0000028623.41308.e5)
- ↑ Halberkann, J. Ber. 1921, 54, 3090.
See also
Acknowledgement and Attribution Regarding Sources of Content
Some of the initial content on this page may be incorporated in part from copyleft sources in the public domain including wikis such as Wikipedia and AskDrWiki. Drug information for patients came from the The National Library of Medicine. Infectious disease information may have come from the Centers for Disease Control (CDC). Differential Diagnoses are drawn from clinicians as well as an amalgamation of 3 sources: 1.The Disease Database; 2. Kahan, Scott, Smith, Ellen G. In A Page: Signs and Symptoms. Malden, Massachusetts: Blackwell Publishing, 2004:3; 3. Sailer, Christian, Wasner, Susanne. Differential Diagnosis Pocket. Hermosa Beach, CA: Borm Bruckmeir Publishing LLC, 2002:7 .
