Solvent incorporated sequential [3 + 2] annulation/substitution reaction of azomethine imines and propargyl sulfur ylide

Abstract

A novel solvent incorporated sequential [3 + 2] cycloaddition/substitution reaction of azomethine imines with propargyl sulfur ylide was developed. In the actual three-component reaction, propargyl sulfur ylide acts as a dipole reagent to furnish the annulation with azomethine imines, followed by the protic solvents acting as nucleophiles. The simple, mild, catalyst-free and practical protocol allows for the formation of N,N-bicyclic pyrazolidinones in moderate to excellent yields. Further transformation and gram-scale operations could also be achieved efficiently.