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5-Hydroxypentylammonium acetate as a reusable ionic liquid catalyzes tandem Knoevenagel-phospha-Michael reaction of aldehydes, malononitrile and phosphites

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Abstract

5-Hydroxypentylammonium acetate as a task-specific ionic liquid promotes efficient tandem Knoevenagel-phospha-Michael reaction of phosphite esters with aryl/heteroaryl/alkyl/salicylaldehydes and malonitrile/ethyl cyanoacetate at room temperature in short reaction times. This simple procedure allows a series of β-phosphonomalonates and 4-substituted 2-amino-4H-chromenes with phosphonic acid dialkyl esters to be synthesized in good to high yields in the presence of an ionic liquid for the first time.

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Scheme 1
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Notes

  1. After adding H2O (10 mL) to the reaction mixture, it was washed with EtOAc (3 × 10 mL). The separated organic layer was dried over Na2SO4 and filtered. Evaporation of the filtrate produced almost pure product which was purified by plate chromatography eluted with n-hexane:EtOAc (1:3).

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  1. Department of Chemistry, College of Sciences, Birjand University, 414, Birjand, Iran

    S. Sobhani & M. Honarmand

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  1. S. Sobhani
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  2. M. Honarmand
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Sobhani, S., Honarmand, M. 5-Hydroxypentylammonium acetate as a reusable ionic liquid catalyzes tandem Knoevenagel-phospha-Michael reaction of aldehydes, malononitrile and phosphites. J IRAN CHEM SOC 9, 661–669 (2012). https://doi.org/10.1007/s13738-012-0088-1

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  • DOI: https://doi.org/10.1007/s13738-012-0088-1

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