General Synthesis of Fully Substituted 4-Aminooxazoles from Amides and 1,4,2-Dioxazol-5-ones Based on Amide Activation and Umpolung Process

A general and efficient synthesis of fully substituted 4-aminodixazoles was developed based on the strategies of amide activation and umpolung reaction. In this method, 1,4,2-dioxazol-5-ones were introduced as a rare type of umpolung reagent bearing a nucleophilic N-atom that could be used well together with the activating agent Tf2O. Because 1,4,2-dioxazol-5-ones played triple roles as an umpolung reagent, a substrate, and a weak base, the method proceeded smoothly under extremely convenient conditions.

Automated summary

A general and efficient synthesis of fully substituted 4-aminodixazoles was developed using amide activation and umpolung reaction strategies. 1,4,2-dioxazol-5-ones were introduced as a rare type of umpolung reagent with a nucleophilic N-atom, allowing smooth reaction under convenient conditions.