Mannich Reaction

The Mannich reaction is an organic reaction which consists of an amino alkylation of an acidic proton placed next to a carbonyl functional group with formaldehyde and ammonia or any primary or secondary amine. The final product is a β-amino-carbonyl compound also known as a Mannich base. Reactions between aldimines and α-methylene carbonyls are also considered Mannich reactions because these imines form between amines and aldehydes. The reaction is named after chemist Carl Mannich.

The Mannich reaction is an example of 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 the second step in a electrophilic addition with a compound containing an acidic proton(which is, or had become an enol). The Mannich reaction is also considered a condensation reaction.

In the Mannich reaction, ammonia or primary or secondary amines are employed for the activation of formaldehyde. Tertiary amines lack an N-H proton to form the intermediate imine. α-CH-acidic compounds (nucleophiles) include carbonyl compounds, nitriles, acetylenes, aliphatic nitro compounds, α-alkyl-pyridines or imines. It is also possible to use activated phenyl groups and electron-rich heterocycles such as furan, pyrrole, and thiophene. Indole is a particularly active substrate; the reaction provides gramine derivatives.

Read more about Mannich Reaction:  Reaction Mechanism, Asymmetric Mannich Reactions, Applications

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Alkaloid - Biosynthesis - Mannich Reaction
... An integral component of the Mannich reaction, in addition to an amine and a carbonyl compound, is a carbanion, which plays the role of the nucleophile in the nucleophilic addition to the ion formed by the ... The Mannich reaction can proceed both intermolecularly and intramolecularly ...
Mannich Reaction - Applications
... The Mannich-Reaction is employed in the organic synthesis of natural compounds such as peptides, nucleotides, antibiotics, and alkaloids (e.g ... The Mannich reaction is also used in the synthesis of medicinal compounds e.g ... rolitetracycline (Mannich base of tetracycline), fluoxetine (antidepressant), tramadol, and tolmetin (anti-inflammatory drug) ...

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