Synthesis and characterization of new symmetric bis-1,4-disubstituted-1,2,3-triazole compounds

The 1,4-disubstituted-1,2,3-triazole ring system is a bioactive structural component found in the structure of many compounds and synthesized by researchers for different purposes. Although it is the structural motif of many chemotherapeutic agents, it is also known to have activities such as antituberculosis, anti-inflammatory, antimicrobial, antifungal, xanthine oxidase inhibitor, anticholinesterase, antimalarial and antiviral. It is used in a wide variety of areas because it has bioactivity and a stable structure. In the synthesis of triazole compounds, the method preferred by researchers is the Cu(I) catalyzed 1,3-dipolar cycloaddition reaction of azides and alkynes (CuAAC). Within the scope of this thesis, new symmetric bis-1,2,3-triazole compounds (130a-f) containing two 1,2,3-triazole ring systems in a single molecule were synthesized by the CuAAC method. Structures of all synthesized compounds; It was determined by FT-IR, 1H-NMR, 13C-NMR, and HR-ESI-MS analyses. For the synthesis of target products, 2-chloro-N-phenylacetamide derivatives 125a-f were obtained from the reaction of various aniline derivative compounds with chloroacetylchloride, and then 2-azido-N-phenylacetamide 126a-f derivatives were obtained by performing the displacement reactions of 125a-f compounds with NaN3. On the other hand, phthalic acid (128) was synthesized by the hydrolysis of isobenzofuran-1,3-dione (97) in an acidic environment, and then the bis-terminal alkyne compound (129) was synthesized by the reaction of 128 with propargyl bromide. In the last step, the target products, the new symmetric bis-1,2,3-triazole compounds 130a-f, were successfully synthesized using the CuAAC method of compounds 129 and 126a-f.