Tandem Knoevenagel–Michael reactions in aqueous diethylamine medium: A greener and efficient approach toward bis-dimedone derivatives
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 p...
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| Series: | Arabian Journal of Chemistry |
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| Online Access: | http://www.sciencedirect.com/science/article/pii/S1878535214000768 |
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doaj-16f4901a883e4483b7d34a7cfcc4a7732020-11-24T20:51:33ZengElsevierArabian Journal of Chemistry1878-53522017-02-0110218519310.1016/j.arabjc.2014.04.008Tandem Knoevenagel–Michael reactions in aqueous diethylamine medium: A greener and efficient approach toward bis-dimedone derivativesAbdullah Mohammed Al-Majid0Mohammad Shahidul Islam1Assem Barakat2Nasser J. Al-Qahtani3Sammer Yousuf4M. Iqbal Choudhary5Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaKing Abdulaziz City for Science and Technology, P.O. Box 6086, Riyadh 11442, Saudi ArabiaH.E.J. Research Institute of Chemistry, International Center for Chemical Sciences, University of Karachi, Karachi 75270, PakistanDepartment of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi ArabiaDiethylamine 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 (15–60 min). 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) Å, b = 18.0995(15) Å, c = 15.8615(13) Å, α = 90°, β = 107.975(2)°, γ = 90°, V = 2809.8(4) Å3, and Z = 4. Compound 3c crystallizes in the monoclinic space group P 21/n with a = 10.2816(16) Å, b = 18.080(3) Å, c = 15.637(2) Å, α = 90°, β = 107.076(4)°, γ = 90°, V = 2778.6(7) Å3, 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.http://www.sciencedirect.com/science/article/pii/S1878535214000768Tandem Knoevenagel–Michael reactionsMCRsAqueous mediaDimedoneZwitterions |
| collection |
DOAJ |
| language |
English |
| format |
Article |
| sources |
DOAJ |
| author |
Abdullah Mohammed Al-Majid Mohammad Shahidul Islam Assem Barakat Nasser J. Al-Qahtani Sammer Yousuf M. Iqbal Choudhary |
| spellingShingle |
Abdullah Mohammed Al-Majid Mohammad Shahidul Islam Assem Barakat Nasser J. Al-Qahtani Sammer Yousuf M. Iqbal Choudhary Tandem Knoevenagel–Michael reactions in aqueous diethylamine medium: A greener and efficient approach toward bis-dimedone derivatives Arabian Journal of Chemistry Tandem Knoevenagel–Michael reactions MCRs Aqueous media Dimedone Zwitterions |
| author_facet |
Abdullah Mohammed Al-Majid Mohammad Shahidul Islam Assem Barakat Nasser J. Al-Qahtani Sammer Yousuf M. Iqbal Choudhary |
| author_sort |
Abdullah Mohammed Al-Majid |
| title |
Tandem Knoevenagel–Michael reactions in aqueous diethylamine medium: A greener and efficient approach toward bis-dimedone derivatives |
| title_short |
Tandem Knoevenagel–Michael reactions in aqueous diethylamine medium: A greener and efficient approach toward bis-dimedone derivatives |
| title_full |
Tandem Knoevenagel–Michael reactions in aqueous diethylamine medium: A greener and efficient approach toward bis-dimedone derivatives |
| title_fullStr |
Tandem Knoevenagel–Michael reactions in aqueous diethylamine medium: A greener and efficient approach toward bis-dimedone derivatives |
| title_full_unstemmed |
Tandem Knoevenagel–Michael reactions in aqueous diethylamine medium: A greener and efficient approach toward bis-dimedone derivatives |
| title_sort |
tandem knoevenagel–michael reactions in aqueous diethylamine medium: a greener and efficient approach toward bis-dimedone derivatives |
| publisher |
Elsevier |
| series |
Arabian Journal of Chemistry |
| issn |
1878-5352 |
| publishDate |
2017-02-01 |
| description |
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 (15–60 min). 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) Å, b = 18.0995(15) Å, c = 15.8615(13) Å, α = 90°, β = 107.975(2)°, γ = 90°, V = 2809.8(4) Å3, and Z = 4. Compound 3c crystallizes in the monoclinic space group P 21/n with a = 10.2816(16) Å, b = 18.080(3) Å, c = 15.637(2) Å, α = 90°, β = 107.076(4)°, γ = 90°, V = 2778.6(7) Å3, 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. |
| topic |
Tandem Knoevenagel–Michael reactions MCRs Aqueous media Dimedone Zwitterions |
| url |
http://www.sciencedirect.com/science/article/pii/S1878535214000768 |
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