Mannich reaction
| Mannich reaction | |
|---|---|
| Named after | Carl Mannich |
| Reaction type | Coupling reaction |
| Identifiers | |
| Organic Chemistry Portal | mannich-reaction |
| RSC ontology ID | RXNO:0000032 |
In organic chemistry, the Mannich reaction is a three-component organic reaction that involves the amino alkylation of the α-position of a ketone or aldehyde with an aldehyde and a nullary, primary, or secondary amine (−NH2).[1] The final product is a β-amino-carbonyl compound also known as a Mannich base. The reaction is named after Carl Mannich.[2][3]
The Mannich reaction starts with the nucleophilic addition of an amine to a carbonyl group followed by dehydration to the Schiff base. The Schiff base is an electrophile which reacts in a second step in an electrophilic addition with an enol formed from a carbonyl compound containing an acidic α-proton. The Mannich reaction is a condensation reaction.[4]: 140
- ^ Smith, Michael B.; March, Jerry (2007). March's Advanced Organic Chemistry (6th ed.). John Wiley & Sons. pp. 1292–1295. ISBN 978-0-471-72091-1.
- ^ Carl Mannich; Krösche, W. (1912). "Ueber ein Kondensationsprodukt aus Formaldehyd, Ammoniak und Antipyrin". Archiv der Pharmazie (in German). 250 (1): 647–667. doi:10.1002/ardp.19122500151. S2CID 94217627.
- ^ Blicke, F. F. (2011). "The Mannich Reaction". Organic Reactions. 1 (10): 303–341. doi:10.1002/0471264180.or001.10. ISBN 978-0471264187.
- ^ Carey, Francis A.; Sundberg, Richard J. (2007). Advanced Organic Chemistry: Part B: Reactions and Synthesis (5th ed.). New York: Springer. pp. 140–142. ISBN 978-0387683546.