Substituted Diaziridines via [2 + 1] Annulation of Dialkyl Azodicarboxylates with Diazo Esters and In Situ Pyridinium Ylides

Herein, we report the [2 + 1] annulation reactions of dialkyl azodicarboxylate with various diazoesters and in situ generated pyridinium ylides, resulting in the formation of substituted diaziridines in high yields. Notably, these reactions are conducted without any acids, bases, metal catalysts, or photosensitizers, demonstrating a robust strategy for synthesizing structurally diverse diaziridines. Furthermore, the diaziridines can be treated in situ with a variety of arenes, natural products, and pharmaceutical compounds, yielding a range of substituted hydrazine conjugates.