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

1338Department of Chemistry, Yildiz Technical University, Faculty of Science and Arts, Davutpasa Campus, 34220, Esenler, Istanbul, Turkey

2338Institute of Organic Chemistry, University of Technology, Leibnizstr. 6, Clausthal, D-38678, Clausthal-Zellerfeld, Germany

Citation Information: Chemical Papers. Volume 67, Issue 6, Pages 643–649, ISSN (Online) 1336-9075, DOI: 10.2478/s11696-013-0338-4, March 2013

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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

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