Synthesis of bis-1,2,3-triazolyl ligands and their metal complexes

Cilj ovog rada bila je sinteza bis-1,2,3-triazolnih liganada i njihovih metalnih kompleksa. U radu su uz bis-1,2,3-triazolne ligande priređeni i mono-1,2,3-triazolni ligandi te njihovi metalni kompleksi. 1,2,3-triazolni ligandi 3a, 3b, 6a, 6b, 10a, 10b, 14a, 14b, 18a, 18b, 18c i 19 priređeni su bakrom kataliziranom 1,3-dipolarnom cikloadicijom alkina i azida. „Klik“ reakcije provedene su klasičnim metodama organske sinteze te mikrovalovima potpomognutim reakcijama. Spojevi 3a, 3b, 10a, 10b, 14a i 14b korišteni su kao ligandi u sintezi metalnih kompleksa 29, 30, 31, 32, 33, 34, 35, 36, 37, 38 i 39. Ligand 10a je, zbog svoje topljivosti i djelotvorne sinteze, korišten za dodatne karakterizacije u sintezi metalnih kompleksa. Kristalna struktura liganda 10a i kompleksa 32 određena je difrakcijom X-zraka na monokristalu. Kompleksi liganda 10a karakterizirani su spektroskopijom NMR, UV/Vis i IR. Metodom M05-2X/6-31+G(d)/LanL2DZ + ECP u vakuumu i otopini acetonitrila izračunata je stabilnost različitih izomera kompleksa Zn2+ i tri različita liganda u omjeru 1:2 (41, 42, 43), čija je struktura temeljena na triazolnoj strukturi liganda 10a. Antiproliferativna ispitivanja spojeva 3a, 3b, 10a, 10b, 14a, 14b, 18a, 18b, 18c i kompleksa 29 su u tijeku.The aim of this work was the synthesis of bis-1,2,3-triazole ligands and their metal complexes. In this work, bis- and mono-1,2,3-triazole ligands and their metal complexes were prepared. 1,2,3-triazole ligands 3a, 3b, 6a, 6b, 10a, 10b, 14a, 14b, 18a, 18b, 18c and 19 were synthesized by copper catalyzed 1,3-dipolar cycloaddition reaction of alkynes and azides. The "click" reactions were carried out using classical synthetic methods and microwave assisted reactions. Compounds 3a, 3b, 10a, 10b, 14a and 14b were used as ligands in the synthesis of metal complexes 29, 30, 31, 32, 33, 34, 35, 36, 37, 38 and 39. Ligand 10a was used for the characterization of metal complexes because of its good solubility and the efficient synthesis. The crystal structures of ligand 10a and complex 32 was determined by single X-ray diffraction. Complexes of ligand 10a was characterized by NMR, UV/Vis and IR spectroscopy. The stability of the different isomers of complexes of Zn2+and three different ligands (41, 42, 43) in the ratio od 1:2, based on the triazole ligand structure 10a, were calculated by the M05-2X / 6-31 + G (d) / LanL2DZ + ECP method in vacuum and acetonitrile solution. Antiproliferative evaluations of prepared compounds 3a, 3b, 10a, 10b, 14a, 14b, 18a, 18b, 18c and complex 29 are in progress