Synthesi̇s of new substi̇tuted polyhalodi̇ene compounds contai̇ni̇ng aromati̇c and heterocycli̇c structures

Organic compounds containing electrophilic C=C bonds are basic crucial building blocks in the synthesis of open-chain, homo- and heterocyclic compounds with potential bioactive properties. New C-C bonds are formed by adding different nucleophiles to these bonds, depending on the reaction parameters. C=C bonds in the electrophilic nitrovinyl group are the most effective regioselective segments of perhalonitro-1,3-butadienes. They are active compounds, especially due to resonance and inductive effects of nitro groups they contain. Some heterocyclic amine compounds with morpholine, piperazine and piperidine structures used in the study are known for their neuroactive properties. For this reason, they are very important organic compounds in the relevant field of pharmaceutical chemistry. The reactions of S-and S,S-substituted perhalonitrobutadienes with various N-nucleophile heterocyclic amine compounds were examined, and new organic compounds expected to show bio- and neuroactive properties were synthesized in the study. In the study, 2-Nitroperchlorobutadiene (1) was reacted with 1-Decanethiol and 1,3-Propanedithiol directly in a solvent-free environment firstly. As a result of the reactions, S-substituted 2-Nitrotetrachloro-1-decylthio-1,3-butadiene (2) and S,S-substituted 2-(1-Nitroallylidene 2,3, 3-trichloro)-1,3-dithiane (3) compounds were gained respectively and used as starting materials which are known before. Then, the reactions of compounds (2) and (3) with some heterocyclic amines were carried out. N,S-disubstituted, N,S,S- and N,N,S-trisubstituted perhalonitro-1,3-butadienes (4-16) which new thioether structures unknown were gained from the reactions. The thirteen compounds gained in this study are new. The purification methods of the synthesized compounds used in this study are crystallization or chromatography. Molecular models of the compounds were identified with different spectroscopic methods of analysis (1H- and 13C-NMR, MS, IR).