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Arabian Journal of Chemistry v.10 no.2, 2017년, pp.185 - 193  

Tandem Knoevenagel-Michael reactions in aqueous diethylamine medium: A greener and efficient approach toward bis-dimedone derivatives

Al-Majid, A.M. ; Islam, M.S. ; Barakat, A. ; Al-Qahtani, N.J. ; Yousuf, S. ; Iqbal Choudhary, M. ;
  • 초록  

    Diethylamine catalyzed tandem Knoevenagel-Michael reactions have been carried out in aqueous medium as an efficient, greener and cost effective process for the simple one-pot synthesis of bis-dimedone derivatives. Reaction of substituted aromatic aldehyde (1 equiv.) and dimedone (2 equiv.), in the presence of aqueous diethylamine medium at room temperature provides bis-dimedone derivatives 3a-n in excellent yields (87-95%) within a very short reaction time (15-60min). All the bis-dimedone derivatives were obtained in high purity and the products were fully characterized by physical and spectroscopic data. The structures of compounds 3b,c were elucidated by single crystal X-ray diffraction technique. Compound 3b crystallizes in the monoclinic space group P 21/n with a=10.2895(9)A, b=18.0995(15)A, c=15.8615(13)A, α=90 o , β=107.975(2) o , γ=90 o , V=2809.8(4)A 3 , and Z=4. Compound 3c crystallizes in the monoclinic space group P 21/n with a=10.2816(16)A, b=18.080(3)A, c=15.637(2)A, α=90 o , β=107.076(4) o , γ=90 o , V=2778.6(7)A 3 , and Z=4. The use of inexpensive, eco-friendly and readily available reagents, easy work-up, and high purity products makes the procedure a convenient and robust method for the synthesis of tandem Knoevenagel-Michael adducts.


  • 주제어

    Tandem Knoevenagel-Michael reactions .   MCRs .   Aqueous media .   Dimedone .   Zwitterions.  

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