DABCO-Catalyzed Mono-/Diallylation of N-Unsubstituted Isatin N,N′-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates

Allylation of N-unsubstituted isatin N,N '-cyclic azomethine imines with Morita-Baylis-Hillman carbonates in the presence of 1-10 mol% DABCO in DCM at room temperature, rapidly gave N-allylated and N, beta-diallylated isatin N,N '-cyclic azomethine imine 1,3-dipoles in moderate to high yields. The reaction features mild reaction conditions, easily practical operation, and short reaction times in most cases. Furthermore, the alkylated products were transformed into novel bicyclic spiropyrrolidine oxoindole derivatives through the [3+2] or [3+3]-cycloaddition with maleimides or Knoevenagel adducts.

Automated summary

The allylation of N-unsubstituted isatin N,N'-cyclic azomethine imines with Morita-Baylis-Hillman carbonates in the presence of 1-10 mol% DABCO in DCM at room temperature resulted in the rapid formation of N-allylated and N, beta-diallylated isatin N,N'-cyclic azomethine imine 1,3-dipoles in moderate to high yields. This reaction offers mild reaction conditions, practical operability, and short reaction times in most cases. Furthermore, the alkylated products can be transformed into novel bicyclic spiropyrrolidine oxoindole derivatives through [3+2] or [3+3]-cycloaddition reactions with maleimides or Knoevenagel adducts.