Selective synthesis and reactivity expansion of α,β-unsaturated geminal diazides

Abstract

α,β-Unsaturated gem-diazides were selectively obtained catalyzed by Yb(TfO)₃ using α,β-unsaturated aldehydes as substrates and TMSN₃ as a nitrogen source under mild and simple conditions in moderate yields without Schmidt rearrangement and allylic rearrangement. The study on the reactivity and application expansion of α,β-unsaturated gem-diazides demonstrated the access to α,β-unsaturated bistriazole, monotriazole, and macrocycle precursors, bis(heterocyclyl)methylene derivatives and imine derivatives with strong electron-withdrawing groups under simple conditions. Compound 9c exhibited antiproliferative activity against A549 which could be a lead compound for the discovery of anticancer agents.