Passerini reaction

The Passerini reaction is a by Italian chemist Luigi Mario Torquato Passerini (* 1891) discovered in 1921 described three-component reaction for the synthesis of esters of α - hydroxycarboxylic acid amides from carbonyl compounds (aldehydes or ketones), isocyanides and carboxylic acids. The Passerini reaction belongs to the group of multi-component reactions.

The Passerini reaction often finds application in combinatorial chemistry. It is one of the chemical reactions that occur with high atom economy.

Reaction mechanism

Between the carbonyl and the acid component is initially form of hydrogen bonds. Subsequently, the carbon atom of the isocyanide attacks the carbonyl carbon of the ketone (R1, R2 = Organylgruppe ) or aldehyde ( R 1 = hydrogen atom, R2 = Organylgruppe or hydrogen atom ) to. In addition, the oxygen atom of the carbonyl group of the carboxylic acid ( R 3 COOH ) is under attack. After a rearrangement within the molecule finally created the product, a carboxylic acid amide.

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