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Amide reduction is a reaction in organic synthesis where an amide is reduced to either an amine or an aldehyde ... Selective catalysts for the reaction include copper ...
Nitrogen derivates such as amides, nitriles, imines, and most other organonitrogen compounds are reduced to the corresponding amines. Nitroarenes can be converted to azoxyarenes, azoarenes, or hydroazoarenes, depending on the reaction conditions. [1] Some common functional group reductions using SMEAH can be found below:
These hydrides facilitate the reduction of imines or iminium ions—key intermediates in reductive amination—into secondary or tertiary amines. This reaction typically occurs under mild conditions with excellent selectivity, which often makes H 2 /Pd the first choice for synthesizing amines in pharmaceuticals and fine chemicals.
The amide will serve as a nucleophile for the cyclization forming the azlactone 4. Deprotonation and acylation of the azlactone forms the key carbon-carbon bond. Subsequent ring-opening of 6 and decarboxylation give the final keto-amide product. [9] [10] The mechanism of the Dakin-West reaction
[13] [14] The ruthenium catalyst has been shown, however, to go through a ruthenium hydride intermediate. The Meerwein–Ponndorf–Verley reduction has also been effected with synthetically useful yield by plutonium (III) isopropoxide. [15] The standard MPV reduction is a homogeneous reaction several heterogeneous reactions have been developed ...
3.1 Hydrogenation catalyst. 4 References. Toggle the table of contents. ... Rhenium trioxide finds some use in organic synthesis as a catalyst for amide reduction. [5]
The catalyst is also used for the hydrogenolysis of phenyl phosphate esters, a reaction that does not occur with palladium catalysts. The pH of the solvent significantly affects the reaction course, and reactions of the catalyst are often enhanced by conducting the reduction in neat acetic acid, or solutions of acetic acid in other solvents.
Amide reduction: Amines, aldehydes Reagent: lithium aluminium hydride followed by hydrolysis Vilsmeier–Haack reaction: Aldehyde (via imine) POCl 3, aromatic substrate, formamide Bischler–Napieralski reaction: Cyclic aryl imine: POCl 3, SOCl 2, etc. Tautomeric chlorination: Imidoyl chloride: Oxophilic halogenating agents, e.g. COCl 2 or SOCl 2