Priprava lipofilnih triazolnih derivata propargilamina klik-reakcijama ; Kemija alkina u novom nastavnom programu kemije

master's thesis

• Title (english): Preparation of lipophilic triazole derivatives of propargylamine by click reactions ; Alkyne chemistry in new chemistry syllabus
• Author: Dominik Hamer
• Mentor: Vesna Petrović Peroković (mentor)
• Mentor: Nenad Judaš (mentor)
• Committee member: Vesna Petrović Peroković (predsjednik povjerenstva)
• Committee member: Nenad Judaš (član povjerenstva)
• Committee member: Mirela Sertić Perić (član povjerenstva)
• Committee member: Ivana Maguire (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Biology); Zagreb
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2020-09-30, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

U okviru istraživačkog dijela diplomskog rada opisana je priprava lipofilnih alifatskih azida (dodecil, heksadecil) te kolesterol-azida potrebnih za sintezu 1,4-disupstituiranih triazolnih derivata. Alifatski azidi pripravljeni su reakcijom supstitucije iz odgovarajućih alkil-bromida i natrijevog azida, dok je kolesterolazid pripravljen iz kolesterol-mesilata. Sva tri azida te prethodno pripravljeni 2-(adamantan-1-il)etil-azid u reakciji s propargilaminom prevedeni su u nove 1,4-disupstituirane... More 1,2,3-triazole bakrom(I) kataliziranom azid-alkinskom 1,3-dipolarnom cikloadicijom (CuAAC). Klik-reakcija provedena je u prisutnosti di-tertbutil- dikarbonata (Boc2O) pri čemu je istodobno zaštićena amino-skupina propargilamina. Uklanjanjem Boc zaštite u prisutnosti trifluoroctene kiseline pripravljeni su triazolni derivati propargilamina, ciljne molekule ovog rada. Struktura svih pripravljenih spojeva potvrđena je uobičajenim analitičkim metodama – spektroskopijom NMR (1H i 13C), infracrvenom spektroskopijom (IR) i spektrometrijom masa (MS). U metodičkom dijelu rada prikazana je usporedba nastavnih sadržaja i udžbenika pisanih prema novom i starom kurikulumu vezanih uz kemiju alkina u osnovnoj i srednjoj školi. Osmišljen je 90-minutni nastavni sat koji se temelji na pokusu i metodi učenja otkrivanjem u kojoj učenici uz nastavnikovu pomoć i pripadajuće nastavne materijale usvajaju nova znanja o kemiji alkina. Less

Abstract (english)

In this diploma thesis preparation of lipophilic aliphatic azides (dodecyl, hexadecyl) and cholesterol azide was described. Prepared azides were further used as precursors in synthesis of 1,4-disubstitued triazole derivatives. Aliphatic azides were prepared by substitution from the corresponding alkyl bromides and sodium azide. Cholesterol azide was prepared from mesylate derivative. All azides as well as previously prepared 2-(adamantan-1-yl)ethyl azide were transformed into
1,4-disubstitued... More 1,2,3-triazoles using copper(I) catalyzed azide-alkyne 1,3-dipolar cycloaddition (CuAAC) with commercially available propargylamine. di-tert-butyl dicarbonate (Boc2O) was also used in click reaction in order to protect amino group of propargylamine in the same step. Boc group removal with trifluoroacetic acid was carried out next and target molecules, the triazole derivatives of propargylamine, were obtained. The structures of all prepared compounds were confirmed using standard analytical methods - NMR spectroscopy (1H and 13C), infrared spectroscopy (IR) and mass spectrometry (MS). In methodical part was given the comparison of old and new chemistry syllabus and textbooks concerning alkyne chemistry in elementary and high school. A 90-minute lesson based on experiment and inquiry learning was proposed in which students, with help from teacher and accompanying teaching materials, acquire new knowledge about alkyne chemistry. Less

• Keywords: azidi; 1; 3-dipolarna cikloadicija; kemija alkina; klik-reakcije; nastavni kurikulum; propargilamin; 1; 2; 3-triazoli; učenje otkrivanjem
• Keywords (english): alkyne chemistry; azides; click reactions; 1; 3-dipolar cycloaddition; inquiry learning; propargylamine; teaching curriculum; 1; 2; 3-triazoles
• Language: croatian
• URN:NBN: urn:nbn:hr:217:036634
• Study programme: Title: Integrated undergraduate and graduate university study of Biology and Chemistry Education; specializations in: Integrated undergraduate and graduate university study of Biology and Chemistry Education; Course: Integrated undergraduate and graduate university study of Biology and Chemistry Education; Study programme type: university; Study level: integrated undergraduate and graduate; Academic / professional title: magistar/magistra edukacije biologije i kemije (magistar/magistra edukacije biologije i kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Open access; Embargo expiration date: 2022-09-30
• Created on: 2020-10-27 08:34:25