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Encyclopedia > Mannich base

A mannich base is the reaction product of an amine and a carbonyl compound that engage in a nucleophilic addition reaction followed by elimination to the imine salt. It is an intermediate in the Mannich reaction. Ammonia Amines are organic compounds containing nitrogen as the key atom in the amine functional group. ... In chemistry, a carbonyl group is a functional group composed of an atom of carbon double-bonded to an atom of oxygen. ... Nucleophilic addition involves the addition of a nucleophile to a chemical compound. ... An elimination reaction is a type of organic chemical reaction in which two groups are removed from a molecule in either a one or two-step mechanism. ... An imine is the functional group or compound containing the functional group of a carbon-nitrogen double bond. ...


Step 1. A secondary amine reacts with formaldehyde to a mesomeric stabilised carbenium-immonium ion


References

  • Mannich base applied in this example: BELINELO, Valdenir J., REIS, Genuína T., STEFANI, Guglielmo M. et al. Synthesis of 6alpha,7beta-dihydroxyvouacapan-17beta-oic acid derivatives. Part IV: mannich base derivatives and its activities on the electrically stimulated Guinea-pig ileum preparation. J. Braz. Chem. Soc., Nov./Dec. 2002, vol.13, no.6, p.830-837. ISSN 0103-5053. [1] (http://www.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532002000600016) open access publication

  Results from FactBites:
 
Medscape MEDLINE search: Mannich Bases (1049 words)
Some mono Mannich bases (1-phenyl-3-amino-1-propanone salts) and bis Mannich bases (1-phenyl-3-amino-2-amino-methyl-1-propanone salts) derived from acetophenone and a few representative quaternary derivatives were synthesised and their cytotoxicity was tested using the brine shrimp bioassay.
The effect of the acetophenone derived mono Mannich bases 1-3 and bis Mannich base 7 (bis derivative of compound 3) on cellular glutathione level was investigated in Jurkat cells.
This manuscript reports the synthesis of two series of Mannich Bases 3-12 and 21-40 obtained respectively by the reaction of either 2-ethoxycarbonylindoles 1-2 or 5H-pyridazino [4,5b]inoles 17-20 as a substrate with formalin and the appropriate 2 degrees amines under the suitable Mannich conditions.
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