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

Lan-Lan Song; Cheng Yang; Ya-Qin Yu; Da-Zhen Xu

doi:10.1055/s-0036-1588357

Synthesis, Inhaltsverzeichnis

Synthesis 2017; 49(07): 1641-1647
DOI: 10.1055/s-0036-1588357

paper

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

Lan-Lan Song

^aNational Pesticide Engineering Research Center (Tianjin), State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. of China eMail: xudazhen@nankai.edu.cn

,

Cheng Yang

^aNational Pesticide Engineering Research Center (Tianjin), State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. of China eMail: xudazhen@nankai.edu.cn

,

Ya-Qin Yu*

^bKey Laboratory for Water Environment and Resources, Tianjin Normal University, Tianjin, 300387, P. R. of China eMail: yuyaqin@mail.tjnu.edu.cn

,

Da-Zhen Xu*

^aNational Pesticide Engineering Research Center (Tianjin), State Key Laboratory and Institute of Elemento-Organic Chemistry, College of Chemistry, Nankai University, Tianjin 300071, P. R. of China eMail: xudazhen@nankai.edu.cn

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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 reaction

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