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Multicomponent Reactions
Synthesis of thioamides

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.


Mechanism of the Willgerodt-Kindler Reaction

 

Recent Literature


Efficient Synthesis of Thiobenzanilides by Willgerodt-Kindler Reaction with Base Catalysts
K. Okamoto, T. Yamamoto, T. Kanbara, Synlett, 2007, 2687-2690.


Preparation of Thioamide Building Blocks via Microwave-Promoted Three-Component Kindler Reactions
O. I. Zubruyev, N. Stiasni, C. O. Kappe, J. Comb. Chem., 2003, 5, 145-148.