Solvent-Controlled, Tunable Domino Reaction of 3‑Ylideneoxindoles with in Situ-Generated α‑Aryldiazomethanes: A Facile Access to 3‑Spirocyclopropyl-2-oxindole and Pyrazoloquinazolinone Scaffolds

A mild and efficient
solvent-controlled, metal-free switchable
1,3-dipolar cycloaddition/ring contraction or ring expansion domino
reaction of 3-ylideneoxindoles with in situ-generated α-aryldiazomethanes
has been developed. This domino reaction provided a series of aryl-substituted
3-spirocyclopropyl-2-oxindoles and pyrazoloquinazolinones with excellent
regio- and diastereoselectivity from common substrates under varying
solvent conditions.