A Simple and Green Tandem Knoevenagel–Phospha-Michael Reaction for One-Pot Synthesis of 2-Oxindol-3-ylphosphonates Catalyzed by a DABCO-Based Ionic Liquid

Abstract

A simple, clean, and efficient approach for the one-pot synthesis of 2-oxindol-3-ylphosphonates has been successfully developed. With 7 mol% loading of the 1,4-diazabicyclo[2.2.2]octane-based ionic liquid catalyst, 2-oxindol-3-ylphosphonates form in good to excellent yields within short times. This tandem reaction involves a phospha-Michael­ addition to the activated alkenes, which form in situ by Knoevenagel­ condensation. The corresponding products are easily separated and purified by simple crystallization. The catalyst can be recycled five times without significant activity loss. This approach is readily amenable to large-scale synthesis.

Keywords

phosphonates - oxindoles - ionic liquid - Knoevenagel condensation - phospha-Michael addition - tandem reaction

• References

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