K₂CO₃-Promoted Formal [3+3]-Cycloaddition of <i>N</i>-Unsubstituted Isatin <i>N</i>,<i>N′</i>-Cyclic Azomethine Imine 1,3-Dipoles with Knoevenagel Adducts

Abstract

The synthesis of dicyclic spiropyridazine oxoindole derivatives by using [3+3]-cycloaddition of N-unsubstituted isatin N,N′-cyclic azomethine imine 1,3-dipoles was reported. The products bearing two consecutive stereocenters, including spiroquaternary stereocenters in one ring structure, can be effectively obtained in moderate to excellent yields (20–93%) and low to moderate diastereoselectivities (1:9–10:1 dr). The synthesized compounds (>35 examples) were characterized by single-crystal XRD, FTIR, NMR, and mass spectral analysis.

Keywords

• azomethine ylide
• cycloaddition
• Knoevenagel adduct
• spiropyridazine oxoindole
• synthesis