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In organic chemistry, the Mannich reaction is a three-component organic reaction that involves the amino alkylation of an acidic proton next to a carbonyl (C=O) functional group by formaldehyde (H−CHO) and a primary or secondary amine (−NH 2) or ammonia (NH 3). [1] The final product is a β-amino-carbonyl compound also known as a Mannich base.
Generally, a Mannich reaction is the combination of an amine, a ketone with a β-acidic proton and aldehyde to create a condensed product in a β-addition to the ketone. This occurs through an attack on the ketone with a suitable catalytic-amine unto its electron-starved carbon, from which an imine is created.
A Mannich base is a beta-amino-ketone, which is formed in the reaction of an amine, formaldehyde (or an aldehyde) and a carbon acid. [1] The Mannich base is an endproduct in the Mannich reaction, which is nucleophilic addition reaction of a non-enolizable aldehyde and any primary or secondary amine to produce resonance stabilized imine (iminium ion or imine salt).
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In 2017 an IRED was discovered that catalyzed both steps of reductive amination of a wide scope of ketone-amine pairs. [8] These are dubbed reductive aminases (RedAms). [ 1 ] [ 2 ] Engineered RedAms have been employed in industrial processes to support production of pharmaceuticals for clinical trials and commercial manufacturing.
Usually, the amine reacts as the nucleophile with another organic compound acting as the electrophile. This sense of reactivity may be reversed for some electron-deficient amines, including oxaziridines, hydroxylamines, oximes, and other N–O substrates. When the amine is used as an electrophile, the reaction is called electrophilic amination.
The addition of hydrogen and an amino group (NR 2) using reagents other than the amine HNR 2 is known as a "formal hydroamination" reaction. Although the advantages of atom economy and/or ready available of the nitrogen source are diminished as a result, the greater thermodynamic driving force, as well as ability to tune the aminating reagent ...
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