Willgerodt-Kindler Reaction

The Willgerodt Reaction allows the synthesis of amides from aryl ketones under the influence of a secondary amine and a thiating agent. The mechanism involves the formation of an enamine which undergoes thiation, and the carbonyl group migrates to the end of the chain via a cascade of thio-substituted iminium-aziridinium rearrangements.

The Kindler Modification is more convenient:

Hydrolysis of the thioamide provides the amide.

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Mechanism of the Willgerodt-Kindler Reaction

Recent Literature

Efficient Synthesis of Thiobenzanilides by Willgerodt-Kindler Reaction with Base Catalysts

Preparation of Thioamide Building Blocks via Microwave-Promoted Three-Component Kindler Reactions