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Synthesis of new aryl(hetaryl)-substituted tandospirone analogues with potential anxiolytic activity via reductive Heck type hydroarylations

Omer Tahir Gunkara, Bilgesu Onur Sucu, Nuket Ocal, and Dieter E. Kaufmann

Department of Chemistry, Yildiz Technical University, Faculty of Science and Arts, Davutpasa Campus, 34220, Esenler, Istanbul, Turkey

 

E-mail: nocal@yildiz.edu.tr

Abstract: Tandospirone (I), developed as an anxiolytic drug, is an aryl-piperazine compound that binds to both 5-HT1A and dopamine D4 receptors. Palladium-catalysed hydroarylation reactions of tandospirone analogues containing an oxygen bridge and 3-(trifluoromethyl)phenyl or 2,3-dichlorophenyl groups were studied in order to find a new stereoselective access to a series of new exo-aryl(hetaryl)-substituted derivatives with potential biological activity.

Keywords: tandospirone – arylpiperazines – C-C coupling – hydroarylation – heterocycles

Full paper is available at www.springerlink.com.

DOI: 10.2478/s11696-013-0338-4

 

Chemical Papers 67 (6) 643–649 (2013)

Friday, March 29, 2024

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