Pd/C-mediated arylation followed by I2-catalyzed hydration strategy: preparation of functionalized novel indanone derivatives

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

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2 Citations (Scopus)

Abstract

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 

Original languageEnglish
Pages (from-to)1466-1474
Number of pages9
JournalSynthetic Communications
Volume44
Issue number10
DOIs
Publication statusPublished - 19 May 2014
Externally publishedYes

Keywords

  • Alkyne
  • hydration
  • indanone
  • iodine
  • Pd/C

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