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Sinteza monosubstituiranih 'klik' triazolov
Jankovič, Dominik (Author), Gazvoda, Martin (Mentor) More about this mentor... This link opens in a new window

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Abstract
V delu smo se ukvarjali z razvojem enostavne in učinkovite z bakrom(I) katalizirane cikloadicijske reakcije za pripravo 4-monosubstituiranih-1,2,3-triazolov iz terminalnih alkinov in hidrazojske kisline (HN3). Hidrazojsko kislino smo tvorili in situ iz natrijevega azida in Brønstedtove kisline. Reakcije smo zaradi potencialno nevarne HN3 izvajali na zelo majhni količini izhodnih substratov. Na modelni reakciji s fenilacetilenom smo pregledali vpliv reakcijskih parametrov na izkoristek reakcije. Preiskovali smo ustrezno kislino za in situ tvorbo hidrazojske kisline iz natrijevega azida, bakrov katalizator in njegovo optimalno količino, topilo, temperaturo ter čas reakcije. Najboljše rezultate za cikloadicijo med acetilenom in hidrazojsko kislino smo dobili z uporabo žveplove kisline, bakrovga(II) sulfata pentahidrata ob prisotnosti natrijevega askorbata (CuSO4×5H2O/Na(asc)), pri temperaturi 100 °C, reakcijskem času 24 ur, v mešanici topil tetrahidrofuran/voda/etanol. Z razvito katalitsko metodo smo pripravili serijo 4-alkil in 4-(hetero)aril-1,2,3-triazolov. Pripravljenim triazolom smo določili temperaturo tališča, njihovo strukturo potrdili z NMR spektroskopijo in HRMS, njihovo čistost pa s HPLC analizo.

Language:Slovenian
Keywords:1, 2, 3-triazoli, cikloadicija, baker, hidrazojska kislina
Work type:Master's thesis/paper (mb22)
Tipology:2.09 - Master's Thesis
Organization:FKKT - Faculty of Chemistry and Chemical Technology
Year:2020
COBISS.SI-ID:27838723 This link opens in a new window
Views:267
Downloads:65
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Secondary language

Language:English
Title:Synthesis of monosubstituted 'click' triazoles
Abstract:
This thesis describes development of a simple and efficient copper(I)-catalyzed cycloaddition reaction for the synthesis of 4-monosubstituted-1,2,3-triazoles from terminal acetylenes and hydrazoic acid (HN3). Hydrazoic acid was generated in situ from sodium azide and Brønsted acid. Reactions were preformed on small scale due to the hazardous nature of HN3. On the model reaction, employing phenylacetylene as a model substrate, the influence of different reaction parameters was examined. We optimized reaction conditions and found an appropriate acid for in situ generation of HN3, copper catalyst and its optimal amount, solvent, reaction temperature and reaction time for efficient cycloaddition reaction. The best results were obtained when employing sulphuric acid, copper(II) sulfate pentahydrate in combination with sodium ascorbate as catalytic system (CuSO4×5H2O/Na(asc)), reaction temperature 100 °C, reaction time 24 hours in tetrahydrofurane/water/ethanol solvent system. By employing developed catalytic system we prepared various 4-alkyl and 4-(hetero)aryl-1,2,3-triazoles. Melting points were determined to the prepared triazoles, which were characterised by using NMR spectroscopy and HRMS. Their purity was further analyzed by HPLC analysis.

Keywords:1, 2, 3-triazoles, cycloaddition, copper, hydrazoic acid

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