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Regioselektivna sinteza 1,4-disupstituiranih 1,2,3-triazolnih derivata
Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology, 2016. urn:nbn:hr:149:236880
Gregorić, Tomislav
University of Zagreb
Faculty of Chemical Engineering and Technology

Institutional repository: Repository of Faculty of Chemical Engineering and Technology University of Zagreb

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Gregorić, T. (2016). Regioselektivna sinteza 1,4-disupstituiranih 1,2,3-triazolnih derivata (Master's thesis). Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology. Retrieved from https://urn.nsk.hr/urn:nbn:hr:149:236880

Gregorić, Tomislav. "Regioselektivna sinteza 1,4-disupstituiranih 1,2,3-triazolnih derivata." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2016. https://urn.nsk.hr/urn:nbn:hr:149:236880

Gregorić, Tomislav. "Regioselektivna sinteza 1,4-disupstituiranih 1,2,3-triazolnih derivata." Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, 2016. https://urn.nsk.hr/urn:nbn:hr:149:236880

Gregorić, T. (2016). 'Regioselektivna sinteza 1,4-disupstituiranih 1,2,3-triazolnih derivata', Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, accessed 25 November 2024, https://urn.nsk.hr/urn:nbn:hr:149:236880

Gregorić T. Regioselektivna sinteza 1,4-disupstituiranih 1,2,3-triazolnih derivata [Master's thesis]. Zagreb: University of Zagreb, Faculty of Chemical Engineering and Technology; 2016 [cited 2024 November 25] Available at: https://urn.nsk.hr/urn:nbn:hr:149:236880

T. Gregorić, "Regioselektivna sinteza 1,4-disupstituiranih 1,2,3-triazolnih derivata", Master's thesis, University of Zagreb, Faculty of Chemical Engineering and Technology, Zagreb, 2016. Available at: https://urn.nsk.hr/urn:nbn:hr:149:236880

Metadata
TitleRegioselektivna sinteza 1,4-disupstituiranih 1,2,3-triazolnih derivata
Title (english)Regioselective synthesis of 1,4-disubstituted 1,2,3-triazole derivatives
AuthorTomislav Gregorić
MentorSilvana Raić-Malić (mentor)
Committee memberSilvana Raić-Malić (predsjednik povjerenstva)
Committee memberTatjana Gazivoda Kraljević (član povjerenstva)
Committee memberBruno Zelić (član povjerenstva)
GranterUniversity of Zagreb
Faculty of Chemical Engineering and Technology
Zagreb
Defense date and country2016-06-30, Croatia
Scientific / art field,
discipline and subdiscipline		NATURAL SCIENCES
Chemistry
Organic Chemistry
Abstract
Cilj ovog rada bila je sinteza novih 1,2,3-triazolnih derivata 4,5-didehidro-5,6-dideoksi-L-askorbinske kiseline (5–13) regioselektivnom 1,3-dipolarnom cikloadicijom odgovarajućih terminalnih alkina i C-6-azidnog derivata L-askorbinske kiseline (4). Pored konvencionalne sintetske metode, provedeno je optimiranje "klik" reakcija (14–27) u mikroreaktorskom sustavu uz pomoć ultrazvučnog zračenja pri protoku od 0,5 μl/min i temperaturi od 50 °C. Analiza reakcijskih smjesa primjenom visokoučinkovite tekućinske kromatografije (HPLC) pokazala je da je većina "klik" reakcija provedenih u mikroreaktoru bila uspješnija, uz veća iskorištenja i znatno kraće vrijeme reakcija u odnosu na konvencionalnu sintezu. Triazolnim derivatima 2,3-O,O-dibenzil-4,5-didehidro-5,6-dideoksi-L-askorbinske kiseline (7–9) potom je uklonjena benzilna zaštitna skupina pomoću boron-triklorida pri čemu su izolirani spojevi 11–13 sa slobodnim hidroksilnim skupinama. Strukture svih sintetiziranih spojeva potvrđene su spektroskopijom 1H- i 13C-NMR. Novosintetiziranim spojevima ispitat će se antitumorska aktivnost na više tumorskih staničnih linija porijeklom iz čovjeka, a spojevima sa slobodnim hidroksilnim skupinama (11–13) ispitat će se i antioksidativna aktivnost.
Abstract (english)
The aim of this work was the synthesis of new 1,2,3-triazole 4,5-didehydro-5,6-dideoxy-L-ascorbic acid derivatives (5–13) using regioselective 1,3-dipolar cycloaddition of the corresponding terminal alkynes and C-6-azido L-ascorbic acid derivative (4). Besides the conventional synthetic approach, reactions of "click" chemistry were optimized in a microreactor at a flow rate of 0.5 μL/min and 50 °C under ultrasonic irradiation (14–27). The analysis of reaction mixtures by high performance liquid chromatography (HPLC) demonstrated that most of the click reactions in microreactors were more efficient and proceeded with higher yields and shorter reaction time than those for conventional syntheses. The benzyl groups from the triazole 2,3-O,O-dibenzyl-4,5-didehydro-5,6-dideoxy-L-ascorbic acid derivatives 7–9 were remowed using boron trichloride and compounds (11–13) with free hydroxyl groups were obtained. The structures of all synthesized compounds were determined by 1H- and 13C-NMR spectroscopy. The novel compounds will be evaluated for their antitumor activity in several human tumor cell lines and antioxidant capacity of compounds (11–13) with free hydroxyl groups will be also tested.
Keywords
Keywords (english)
Languagecroatian
URN:NBNurn:nbn:hr:149:236880
Study programmeTitle: Applied Chemistry - Graduate 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: graduate
Academic / professional title: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
Type of resourceText
File originBorn digital
Access conditionsOpen access
Terms of useLicence In copyright icon
Public noteSlužbeni naslov rada je Regioselektivna sinteza 1,4-disupstituiranih 1,2,3-triazolnih derivata, dok je u izvornom diplomskom radu u tekstualnom obliku i u dokumentu u PDF formatu naslov pogrešno napisan kao Regioselektivna sinteza 1,4-disupstituiranih 1,2,3-triazola.
Created on2017-04-14 12:34:03