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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 (−NH2) or ammonia (NH3). [ 1 ] The final product is a β-amino-carbonyl compound also known as a Mannich base.
RXNO:0000232. The Petasis reaction (alternatively called the Petasis borono–Mannich (PBM) reaction) is the multi-component reaction of an amine, a carbonyl, and a vinyl - or aryl - boronic acid to form substituted amines. Reported in 1993 by Nicos Petasis as a practical method towards the synthesis of a geometrically pure antifungal agent ...
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).
Biosynthesis of β-carboline alkaloids occurs through the formation of Schiff base from tryptamine and aldehyde (or keto acid) and subsequent intramolecular Mannich reaction, where the C(2) carbon atom of indole serves as a nucleophile. Then, the aromaticity is restored via the loss of a proton at the C(2) atom. The resulting tetrahydro-β ...
Organocatalysis. In organic chemistry, organocatalysis is a form of catalysis in which the rate of a chemical reaction is increased by an organic catalyst. This "organocatalyst" consists of carbon, hydrogen, sulfur and other nonmetal elements found in organic compounds. [3][4][5][6][7][8] Because of their similarity in composition and ...
The nitro-Mannich reaction (or aza-Henry reaction) is the nucleophilic addition of a nitroalkane (or the corresponding nitronate anion) to an imine, resulting in the formation of a beta-nitroamine. [1] With the reaction involving the addition of an acidic carbon nucleophile to a carbon-heteroatom double bond, the nitro-Mannich reaction is ...
Borylation occurs selectively at the least sterically hindered and least electron rich primary C–H bond in a range of acetals, ethers, amines, and alkyl fluorides. [10] Additionally, no reaction is shown to occur in the absence of primary C–H bonds, for example when cyclohexane is the substrate.
A common undergraduate experiment is the Friedel–Crafts reaction of ferrocene with acetic anhydride (or acetyl chloride) in the presence of phosphoric acid as a catalyst. Under conditions for a Mannich reaction, ferrocene gives N,N-dimethylaminomethylferrocene. Important reactions of ferrocene with electrophiles and other reagents