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DOI: 10.1055/s-0036-1588357
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
Publication History
Received: 23 September 2016
Accepted after revision: 01 November 2016
Publication Date:
06 December 2016 (online)
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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 reactionSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0036-1588357.
- Supporting Information
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