Experimental and Theoretical Investigation of One-pot Synthesis of 2-Amino-4H-chromenes Catalyzed by Basic-functionalized Ionic Liquids

Authors

  • Yuanyuan Wang,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Chemistry Department of East China Normal University, Shanghai 200062, China
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  • Yuetong Wu,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Chemistry Department of East China Normal University, Shanghai 200062, China
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  • Yu Wang,

    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Chemistry Department of East China Normal University, Shanghai 200062, China
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  • Liyi Dai

    Corresponding author
    1. Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Chemistry Department of East China Normal University, Shanghai 200062, China
    • Shanghai Key Laboratory of Green Chemistry and Chemical Processes, Chemistry Department of East China Normal University, Shanghai 200062, China, Tel.: 0086-021-62233037; Fax: 0086-021-62602447
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Abstract

An efficient and environmentally benign procedure for the reactions of three components condensation of salicylaldehyde and two different CH acids to give 2-amino-4H-chromenes catalyzed by a series of basic-functionalized ionic liquids was reported. The most possible reaction pathway was proposed for the first time by performing density functional theory (DFT) calculations. Both cation and anion of [Bmim]OH have a cooperative effect on the reaction. [Bmim]+ increases the electrophilicity of salicylaldehyde via intermolecular hydrogen bonds, while OH deprives proton of two CH acids to strengthen their nucleophilic ability.

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