Tandospirone derivatives hydroarylation reactions

In this century, most of the organic synthesis research are based on the synthesizing new pharmaceutical active agents together with the measurements of these compounds biologically activities to earn as medicines in literature. The researches on the synthesis of tandospirone derivatives, which are having very important biologically and pharmacological activities in the biological systems, are quite too few in the literature. Tandospirone is being used as a medicine and also known as a 5-HT1A receptor with a high affinity binding as an anxiolytic effect and an antidepressant in biological systems. In this study, we practiced synthesis of tandospirone derivatives to open new prospects to the pharmacological researches and these derivatives are predicted as a more effective agent on the nervous system.Moreover, an organic synthesis called Heck Reaction, which is made by arylation of alkenes in presence of palladium catalyst, is a one step reaction for the alkene systems to turn to arylalkane systems. The asymmetric Heck-type hydroarylations have been examined by Prof. Dr. Dieter Kaufmann and our research group intensively, because of the easily obtained stereoselective results. In common research triphenylphosphine is being used for ligand building, but in our researches triphenylarsine has been tried and found successful on increasing the efficiency of the reaction.Furthermore, 1,3-dipolar cycloaddition reactions are known as useful synthesizing methods, especially for developing new chiral centers. Also these reactions include asymmetric synthesis which are having high importance both in pharmacology and agriculture industries. 1,3-dipolar cycloaddition reactions, which are achieved by nitrile oxides, are producing isoxazolines derivatives, having a biological importance. Especially, cycloaddition of nitrile oxides into olefines is considerably interesting, as the resulting isoxazolines are compounds of some important pharmacophores [156], [1].This study is planned as four steps. The first step is the synthesis of starting material N-[4-((4-pyrimidin-2-yl)piperazin-1-yl)butyl]-7-oxabicyclo[2.2.1]hept-5-ene-2-exo,3-exo-dicarboximide. The second step is including hydroarylation reactions of this alkene tandospirone with aryl(hetaryl) iodides. On the third step is based on performing 1,3-dipolar cycloaddition reactions of starting material with nitrile oxides to obtain isoxazoline derivatives. The last step is including structure characterizations of all new compounds by FTIR, 1H NMR, 13C NMR (APT), LC-MS and GC-MS techniques, respectively.