Catalyst-free synthesis of oxazol-2(3H)-ones from sulfilimines and diazo compounds through a tandem rearrangement/aziridination/ring-expansion reaction

Oxazol-2(3H)-ones play a significant role in the fields of organic synthesis and drug development. The classical synthesis of oxazol-2(3H)-one derivatives requires high temperatures, metal catalysts, complex substrates or multi-step reactions. We report a concise synthesis of oxazol-2(3H)-ones from readily available diazo compounds and sulfilimines through a tandem rearrangement/aziridination/ring-expansion reaction in the absence of any catalyst and additive. This reaction is scalable and the obtained products were readily converted to other valuable aza-heterocyclic frameworks.

Automated summary

This novel synthetic method allows for the synthesis of oxazol-2(3H)-ones from common compounds without the need for high temperatures, metal catalysts, or complex substrates. The reaction is efficient and the products obtained can be easily converted into other valuable heterocyclic frameworks.