Mannich Bases: Chemistry and Uses

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Author s : Gheorghe Roman.

DOI : The chemistry and applications of aminomethylated pyrroles are extensively reported by the present review. The scope and limitations of the aldehyde component and amine reagents in the Mannich reaction of pyrroles have been explored, the use of preformed aminomethylation reagents and catalysts with the view to improve yields or stereoselectivity has been surveyed, and the mechanism and by-products arising from the aminomethylation of pyrroles have been outlined.

Pyrrole Mannich bases have been portrayed as excellent H-, C-, N-, O-, S-, and P-alkylating agents as a direct consequence of their ability to replace the easily leaving dialkylamino group with other nucleophiles, and the involvment in ring closure processes leading to porphyrins, or other miscellaneous reactions have also been included in the broad coverage of these compounds reactivity.

Mannich Reaction - Chemistry LibreTexts

A particular attention has been paid to the contribution of pyrrole Mannich bases to drug discovery and advances in medicinal chemistry. Maddila S, Jonnalagadda SB. Lett Drug Des Discov. PMC Canada manuscript submission; Nov;65 11 — Synthesis, anti-HIV and antitubercular activities of lamivudine prodrugs.

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Novel 2- E -substituted benzylidene N-substituted aminomethyl cyclohexanones and cyclohexanols as analgesic and anti-inflammatory agents. Med Chem Res. Springer-Verlag; Aug;22 8 — Arch Pharm Weinheim. Regioselective reaction: Synthesis, characterization and pharmacological activity of some new Mannich and Schiff bases containing sydnone. Synthesis and biological evaluation of some 1,3,4-oxadiazole derivatives. Synthesis, Characterization and Antimicrobial Activity of Novel 3,5-Disubstituted-1,3,4-oxadiazoleones. Rev Chim -Bucharest- Orig Ed.

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Synthesis and antimicrobial studies of some Mannich bases carrying imidazole moiety. Acta Pharm. Bioorg Med Chem.

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    Aminomethylated Pyrroles: Casting a Spotlight

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    Mannich bases in medicinal chemistry and drug design.

    Springer US; May;45 2 — McClements D, Decker E. Lipid oxidation in oil-in-water emulsions: Impact of molecular environment on chemical reactions in heterogeneous food systems. Progress has been made towards asymmetric Mannich reactions. When properly functionalized the newly formed ethylene bridge in the Mannich adduct has two prochiral centers giving rise to two diastereomeric pairs of enantiomers.

    The first asymmetric Mannich reaction with an unmodified aldehyde was carried with S -proline as a naturally occurring chiral catalyst. The reaction product is diastereoselective with a preference for the syn-Mannich reaction when the alkyl substituent on the aldehyde is a methyl group or when the alkyl group the much larger pentyl group.

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    This stereoselectivity is explained in the scheme below. Proline enters a catalytic cycle by reacting with the aldehyde to form an enamine. The two reactants imine and enamine line up for the Mannich reaction with Si facial attack of the imine by the Si-face of the enamine-aldehyde.

    Mannich reaction mechanism

    Relief of steric strain dictates that the alkyl residue R of the enamine and the imine group are antiperiplanar on approach which locks in the syn mode of addition. The enantioselectivity is further controlled by hydrogen bonding between the proline carboxylic acid group and the imine. The transition state for the addition is a nine-membered ring with chair conformation with partial single bonds and double bonds.