Passerini reaction

The Passerini reaction is a three-component reaction (a multi-component reaction ), discovered by the Italian chemist Mario Passerini (1891–1962) and described in 1921, for the synthesis of esters of α-hydroxycarboxamides from carbonyl compounds ( aldehydes or ketones ), isocyanides and carboxylic acids . The Passerini reaction belongs to the group of multicomponent reactions.

The Passerini reaction is often used in combinatorial chemistry . It is one of the chemical reactions that take place with high atom economy .

Reaction mechanism

Hydrogen bonds are initially formed between the carbonyl component and the acid component. The carbon atom of the isocyanide then attacks the carbonyl carbon of the ketone (R ¹ , R ² = organyl group ) or aldehyde (R ¹ = hydrogen atom; R ² = organyl group or hydrogen atom). In addition, the oxygen atom of the carbonyl group of the carboxylic acid (R ³ COOH) is also attacked. After a rearrangement within the molecule, the product is finally formed, a carboxamide :

Individual evidence

1. ^ M. Passerini: In: Gazzetta Chimica Italiana . Volume 51, 1921, p. 126.
2. ^ M. Passerini: In: Gazzetta Chimica Italiana . Volume 51, 1921, p. 181.

literature

• László Kürti , Barbara Czakó: Strategic Applications of Named Reactions in Organic Synthesis . Elsevier Academic Press, Amsterdam 2005 , ISBN 978-0-12-429785-2 .