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 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.

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 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.

• 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