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Zirconium oxide (NP) - ionic liquid as an efficient media for the domino Knoevenagel hetero Diels-Alder reaction with unactivated alkynes |
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| Authors: | Saeed Balalaie Ali Poursaeed Malihe Javan Khoshkholgh Hamid Reza Bijanzadeh Eckardt Wolf |
| Institution: | 1. Peptide Chemistry Research Center, K. N. Toosi University of Technology, P.O. Box 15875-4416, Tehran, Iran;2. Department of Chemistry, Tarbiat Modares University, P. O. Box 14115-175, Tehran, Iran;3. Tofigh Daru Res. & Eng. Co., 61st St. Km 18 Karaj Highway, Tehran, 37515-375, Iran |
| Abstract: | Immobilized ZrO2-nanopowder (NP) in ionic liquid and different organic solvents was used as a suitable Lewis-acid for the synthesis of polycyclic heterocycles which contains pyran-based skeletons. Reaction of O-propargylated salicylaldehyde with active methylene compounds in the presence of ZrO2-NP in ionic liquid proceeds via domino Knoevenagel hetero Diels-Alder reaction of unactivated alkynes to construct the pyran skeleton. Comparison with different ionic liquids and organic solvents showed that the best results were obtained with 1-butyl-3-methylimidazolium nitrate bmim]NO3] because of short reaction times and high yields. Carrying out the reaction under these conditions has advantages such as: high yields, short reaction times and easy work-up. |
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