Chinese Journal of Organic Chemistry >
Synthesis of Novel Hydroxyl-Functionalized Ionic Liquids andApplication in Knoevenagel Condensation
Received date: 2015-01-13
Revised date: 2015-03-19
Online published: 2015-03-24
Supported by
Project supported by the National Science and Technology Ministry (No. 2012BAK30B03) and the Fundamental Research Funds for the Central Universities (Nos. 2232013A3-05, CUSF-DH-D2013048).
Knoevenagel condensation of benzaldehyde with active methylene compounds, such as ethylcyanoacetate and 2,4-thiazolidinedione proceeded very smoothly in novel hydroxyl-functionalized ionic liquids based on 1,4-diazabicyclo- [2.2.2]octane (DABCO) under solvent-free conditions and these ionic liquids afforded the products in excellent yields [β-benzyl-α-cyanoacrylicacidethylester (≥99%) and 5-benzylidene-2,4-thiazolidinedione (92%)]. These reactions were operated simply, and the desired products were separated directly from the reaction mixture without further purification. In addition, the ionic liquids used were regenerated and recycled several times without significant loss of activity. Finally, a plausible reaction mechanism was proposed, and the relevant evidence was given.
Key words： ionic liquids; hydroxyl-functionalized; Knoevenagel condensation
Liu Yuting , Li Rong , Xing Yanjun . Synthesis of Novel Hydroxyl-Functionalized Ionic Liquids andApplication in Knoevenagel Condensation[J]. Chinese Journal of Organic Chemistry, 2015 , 35(7) : 1520 -1525 . DOI: 10.6023/cjoc201501013
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