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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 Publisher



Asgari MS1 ; Rashidi Ranjbar P1 ; Rahimi R2 ; Mahdavi M3
Authors
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Authors Affiliations
  1. 1. School of Chemistry, University College of Chemistry, University of Tehran, PO Box 14155-6455, Tehran, Iran
  2. 2. Department of Chemistry, Iran University of Science and Technology, Narmak, Tehran, 16846-13114, Iran
  3. 3. Department of Medicinal chemistry, Facaulty of Pharmacy and Pharmaceutical Sciences Research Center, Tehran University of Medicinal Sciences Tehran, Iran

Source: Applied Organometallic Chemistry Published:2020


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. © 2019 John Wiley & Sons, Ltd.