Priprava novih N,N-disupstituiranih derivata skvareinske kiseline

master's thesis

• Title (english): Preparation of novel N,N-disubstituted squaric acid derivatives
• Author: Marina Galić
• Mentor: Dragana Vuk (mentor)
• Committee member: Dragana Vuk (predsjednik povjerenstva)
• Committee member: Vilko Mandić (član povjerenstva)
• Committee member: Jérôme Le Cunff (član povjerenstva)
• Granter: University of Zagreb; Faculty of Chemical Engineering and Technology; Zagreb
• Defense date and country: 2021-09-23, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry

Abstract

Cilj ovog rada je pripremiti nove derivate skvareinske kiseline sintezom kroz 3 reakcijska stupnja. U prvome stupnju provedene su reakcije aminacije odgovarajućih amina i halogenida uz n-BuLi pri čemu su izolirani produkti 1 i 2 uz nusprodukt 3. Nakon uspješne sinteze odgovarajućih tercijarnih amina, uslijedilo je skidanje metoksi skupina te uvođenje hidroksilnih skupina pomoću BBr3, pri čemu su uspješno izolirani alkoholi 4 i 5. U posljednjem stupnju sinteze uslijedila je reakcija kondenzacije sa skvareinskom kiselinom pri čemu su izolirani derivati 6 i 7. Izolirani produkti su pročišćeni te spektroskopski okarakterizirani. Također je provedeno ispitivanje na primarnim i sekundarnim aminima s ciljem optimiranja reakcijskih uvjeta u reakcijama alkiliranja i aminacije s ciljem sinteze sekundarnih odnosno tercijarnih amina kao potencijalnih početnih prekursora u sintezi skvareinskih derivata.

Abstract (english)

The aim of this work is to prepare new derivates of squaric acid by synthesis through 3 reaction steps. In the first step, amination reactions of the corresponding amines and halides with n-BuLi were carried out, to obtain products 1 - 3, respectively. After the successful synthesis of the corresponding amines, demethylation reactions with BBr3 occurs, and alcohols 4 and 5 were successfully isolated. In the last step of the synthesis, a condensation reaction with squaric acid took place, whereby derivates 6 and 7 were isolated. The isolated products were purified and spectroscopically characterized. In this work, a study on primary and secondary amines was also performed in order to optimize the reaction conditions in alkylation and amination reactions, with the aim of synthesis of secondary and tertiary amines as potential starting precursors in the synthesis of squarein derivates.

• Keywords: skvareinska kiselina; amini; aminacija; demeteliranje; kondenzacija
• Keywords (english): squaric acid; amines; amination; demethylation; condensation
• Language: croatian
• URN:NBN: urn:nbn:hr:149:227721
• Project: Number: UIP-2019-04-2367; Title: Fenomeni na površini tijekom priprave naprednih nanokompozita infiltracijom i funkcionalizacijom poroznih materijala; Title: Surface limitations in preparing and infiltration of hard porous nanomaterial by soft or liquid precursors for performance enhancing; Acronym: SLIPPERYSLOPE; Leader: Vilko Mandić; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: UIP
• Project: Number: PZS-2019-02-1555; Title: Fotonaponska-geopolimerna fasada: uloga vode-kisika u naprednom sklapanju filmova kompozitnih materijala; Title: Photovoltaic-geopolymer facade: the water-oxygen role in the advanced assembly of layered composite materials; Acronym: PV-WALL; Leader: Vilko Mandić; Jurisdiction: Croatia; Funder: HRZZ; Funding stream: PZS
• Study programme: Title: Applied Chemistry - Graduate study; specializations in: Environmental chemistry and green technologies, Advanced materials and technologies, Applied organic chemistry; Course: Advanced materials and technologies; Study programme type: university; Study level: graduate; Academic / professional title: magistar/magistra primijenjene kemije (magistar/magistra primijenjene kemije)
• Type of resource: Text
• File origin: Born digital
• Access conditions: Closed access
• Created on: 2023-04-14 12:58:11