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Synthesis of Arylidene – Isoquinolinones bearing Combretastatin Skeleton by Cyclocarbopalladation/cross coupling Tandem Heck-Suzuki Miaura Reactions using nano catalyst Pd@Py-IL-SPION |
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| Authors: | Mohammad Sadegh Asgari Parviz Rashidi Ranjbar Rahmatollah Rahimi Mohammad Mahdavi |
| Institution: | 1. School of Chemistry, University College of Chemistry, University of Tehran, Tehran, PO Box 14155-6455 Iran;2. Department of Chemistry, Iran University of Science and Technology, Narmak, Tehran, 16846-13114 Iran;3. Department of Medicinal chemistry, Facaulty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medicinal Sciences Tehran, Iran |
| Abstract: | Cyclocarbopalladation/cross-coupling cascade intramolecular Heck–Suzuki–Miyaura reactions is applied for the first time by palladium immobilized on pyridine-imidazolium ionic liquid supported magnetic iron oxide nanoparticle catalyst (denoted Pd@Py-IL-SPION) for the last step to synthesize trisubstituted arylidene–isoquinolinones derivatives having Combretastatin skeleton. The reaction is performed via propargylamide intermediates prepared by Ugi 4-CR reactions, which undergoes intramolecular Heck–Suzuki–Miyaura domino reaction to produce the desired trisubstituted arylidene-isoquinolinones. The method shows full regio- and stereoselectivity derives from the particular Pd-catalyzed syn-insertion of triple bond. |
| Keywords: | Combretastatin intramolecular heck–Suzuki Miyaura palladium nano catalyst Ugi 4-component reaction Yinamide |