These metrics are regularly updated to reflect usage leading up to the last few days. Mannich bases are compounds containing the nch 2 x moiety, where the central carbon atom is rendered electrophilic by two flanking heteroatoms, one of which is nitrogen. The mannich reaction is the aminoalkylation reaction, involving the condensation of an enolizable carbonyl compound. In general, a mannich reaction is the addition of an enol or enolate nucleophile to an imine electrophile. Ch acidic compound with a nonenolizable aldehyde like formaldehyde and ammonia. The iminium derivative of the aldehyde is the acceptor in the reaction. In 1912, carl mannich has investigated this reaction. Mannich reaction definition of mannich reaction by. Such moieties usually undergo rapid nonenzymatic hydrolysis, for example.
This overview includes a discussion of the scope and limitations of the classical mannich reaction as a prelude to the more recent methodology. Citations are the number of other articles citing this article, calculated by crossref and updated daily. The imine electrophile is usually formed in situ from the reaction of a primary amine with an aldehyde. Traducida del aleman, revisada y corregida por gabriel moner. Studies on mannich bases studies on mannich bases introduction mannich reaction consists of the condensation of ammonia or primarysecondary amine, usually as the hydrochloride, with formaldehyde or other aldehyde, and a compound containing atleast one hydrogen atom of pronounced reactivity. The mannich base is an endproduct in the mannich reaction, which is nucleophilic addition reaction of a nonenolizable aldehyde and any primary or secondary amine to produce resonance stabilized imine iminium ion or imine salt. A mannich base is a betaaminoketone, which is formed in the reaction of an amine, formaldehyde or an aldehyde and a carbon acid. Mannich bases examined as potential prodrugs are generally o mannich bases nch 2 or or n mannich bases nch 2 nr 1 r 2. Descargue como pdf, txt o lea en linea desde scribd. The order of these notes is c, d, e, f, g, a, and b. This multicomponent condensation of a nonenolizable aldehyde, a primary or secondary amine and an enolizable carbonyl compound affords aminomethylated products.