Background: 3-Methyleneisoindolin-1-one derivatives containing a pyridin-2-ylmethyl substituent
on their ring nitrogen were designed as potential bioactive agents. A one-pot synthesis of these
compounds was achieved via sequential C-C coupling, followed by C-Si bond cleavage and subsequent
tandem C-C/C-N bond forming reaction under ultrasound irradiation.
Method: The methodology involved coupling of (trimethylsilyl)acetylene with iodoarenes in the presence
of 10% Pd/C-CuI-PPh3-Et3N in MeOH followed by treating the reaction mixture with K2CO3 in
aqueous MeOH, and finally coupling with 2-iodo-N-(pyridin-2-ylmethyl)benzamide. The in vitro
evaluation of these compounds was performed to identify some initial hit molecules one of which
showed dose dependent inhibition of PDE4B.
Keywords: 3-Methyleneisoindolin-1-one, ultrasound, Pd/C, PDE4, C-Si bond, MeOH.
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