Synthesis and Selected Transformations of 2-Unsubstituted Imidazole N-Oxides Using a Ball-Milling Mechanochemical Approach

Synthetically relevant 2-unsubstituted imidazole N-oxides were obtained by using the ball-milling mechanochemical method. The presented approach extended the scope of the known method and enabled the preparation of hitherto little known N(1)-aryl-substituted derivatives, which are of interest as starting materials for the synthesis of more complex imidazole-based organic materials, generally in good to excellent yields. In addition, selected one-pot mechanochemical transformations including N- and O-alkylations as well as sulfur transfer reactions based on either (3+2)-cycloaddition reaction with 2,2,4,4-tetramethylcyclobutane-1,3-dithione or sulfurization of the transient imidazol-2-ylidenes, generated from corresponding imidazolium salts, were studied. The reported results can be considered as a continuation of long-term studies focused on the synthesis and applications of 2-unsubstituted imidazole N-oxides.

Automated summary

Synthetically relevant 2-unsubstituted imidazole N-oxides were successfully synthesized using the ball-milling mechanochemical method. This approach not only expanded the scope of the known method, but also enabled the preparation of previously little known N(1)-aryl-substituted derivatives. These derivatives are important starting materials for the synthesis of more complex imidazole-based organic materials. Additionally, the study also investigated selected one-pot mechanochemical transformations including N- and O-alkylations as well as sulfur transfer reactions.