1,2,3-triazolom premošteni konjugati kumarina i ferocena: sinteza i spektroskopska karakterizacija

undergraduate thesis

• Title (english): 1,2,3-triazole-bridged coumarin-ferrocene conjugates: synthesis and spectroscopic characterization
• Author: Mara Majić
• Mentor: Tatjana Gazivoda Kraljević (mentor)
• Committee member: Tatjana Gazivoda Kraljević (predsjednik povjerenstva)
• Committee member: Marijana Hranjec (član povjerenstva)
• Committee member: Danijela Ašperger (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2017-09-20, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry; Organic Chemistry

Abstract

U ovom radu opisana je sinteza derivata kumarina i ferocena premoštenih 1,2,3-triazolnim prstenom. Perkinovom reakcijom pripravljen je derivat kumarina 1, koji je potom in situ s NaN3 preveden u 3-azido-4-hidroksikumarin (2). Knoevenagel-ovom reakcijom je sintetiziran 7-hidroksi-4-klormetilkumarin (4), koji je s NaN3 in situ preveden u 4-azidometilni derivat kumarina 5. O-alkiliranjem spoja 2 s propargil-bromidom uz K2CO3 sintetiziran je 3-azido-7-O-propargilkumarin (8). Klik reakcijom kataliziranom bakrom azidokumarina 2, 5, 8 i 4-azidometil-7-metilkumarina s etinilferocenom pripravljeni su derivati kumarina i ferocena premošteni 1,2,3-triazolom (3, 6, 7 i 9). Strukturna i spektroskopska karakterizacija sintetiziranih spojeva provedena je 1H NMR, UV/Vis i fluorimetrijskom spektroskopijom. Elektrokemijska ispitivanja odabranih spojeva provedena su cikličkom voltametrijom.

Abstract (english)

This paper describes synthesis of coumarin derivates and ferrocene linked through 1,2,3-triazole ring. Coumarin derivate 1 was prepared by Perkin reaction, which gave by in situ reaction with NaN3 3-azido-4-hydroxycoumarin (2). 4-Chlorymethyl-7-hydroxycoumarin (4) was synthesized by Knoevenagel reaction, which was then converted in situ to 4-azidomethyl coumarin derivate (5) with NaN3. O-alkylation reaction of compound 2 with propargyl bromide in the presence of K2CO3 afforeded 3-azido-7-O-propargylcoumarin (8). ''Click'' reaction catalyzed with Cu of azidocoumarines 2, 5, 8 and 4-azidomethyl-7-methylcoumarin with ethynylferrocene gave coumarine and ferrocene derivatives bridged by 1,2,3-triazole ring (3, 6, 7 and 9). Structural characterization of synthesized compounds was acomplished using 1H NMR, UV/Vis and fluorimetric spectroscopy. Electrochemical evaluation of corresponding compounds are carried out by cyclic voltammetry.

• Keywords: kumarin; ferocen; 1 2 3-triazol; klik kemija
• Keywords (english): coumarin; ferrocene; 1 2 3-triazole; click chemistry
• Language: croatian
• URN:NBN: urn:nbn:hr:149:406500
• Study programme: Title: Applied Chemistry - Undergraduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry; Course: Applied organic chemistry; Study programme type: university; Study level: undergraduate; Academic / professional title: sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije (sveučilišni/a prvostupnik/prvostupnica (baccalaureus/baccalaurea) primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access
• Created on: 2021-03-16 13:35:02