The Bimolecular Aliphatic Mannich and Related Reactions
作者： Edward F. Kleinman
DOI: 10.1016/B978-0-08-052349-1.00052-4
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摘要: The Mannich reaction is the prototype of carbon-carbon bond forming reactions that involve addition resonance-stabilized carbon nucleophiles to iminium salts and imines. In its original most widely recognized form, consists three components: (i) ammonia, a primary amine, or secondary amine; (ii) nonenolizable aldehyde, usually formaldehyde; (iii) an active methylene compound. These components condense with concomitant release water produce new base, known as ‘Mannich base’, in which hydrogen replaced by aminomethyl group (equation 1). A typical example acetophenone (1), paraformaldehyde (2) piperidine (3) phenyl β-piperidinoethyl ketone (4; equation 2). formation both carbon-nitrogen this aminomethylation process makes extremely useful synthetic transformation. addition, bases have important applications intermediates for other compounds. They also occur natural products such alkaloids lycopodine (5), cocaine (6) elaeocarpine (7)
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