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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
Author(s) -
Asgari Mohammad Sadegh,
Rashidi Ranjbar Parviz,
Rahimi Rahmatollah,
Mahdavi Mohammad
Publication year - 2020
Publication title -
applied organometallic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.53
H-Index - 71
eISSN - 1099-0739
pISSN - 0268-2605
DOI - 10.1002/aoc.5279
Subject(s) - chemistry , intramolecular force , heck reaction , catalysis , suzuki reaction , stereoselectivity , cascade reaction , palladium , coupling reaction , organic chemistry , combinatorial chemistry , stereochemistry , medicinal chemistry
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.