Willgerodt-Kindler Reaction

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, Synlett2007, 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., 20035, 145-148.