Pd/C-Mediated Arylation Followed by I2-Catalyzed Hydration Strategy: Preparation of Functionalized Novel Indanone Derivatives

19 5 2014

Authors: Balakrishna Dulla, Sunder Kumar Kolli, Upendar Reddy Chamakura, Giridhar Singh Deora, R Ramesh Raju, Manojit Pal

A simple and inexpensive synthesis of novel 2-(3-oxo-3-arylpropyl)-2,3-dihydro-1H-inden-1-one derivatives has been achieved via Pd/C-mediated arylation followed by I2-mediated regioselective hydration of 2-(prop-2-ynyl)-2,3-dihydro-1H-inden-1-ones. A wide variety of 3-aryl substituted 2-propynyl indanone derivatives were conveniently prepared by using 10% Pd/C-PPh3-CuI as a catalyst system, some of which were used to prepare the corresponding ketones via alkyne hydration in the presence of catalytic I2. In an in vitro study a representative compound showed inhibition of PDE4B (phosphodiesterase type 4B) and binding with this protein in silico