Endiinski spojevi u višekomponentnim reakcijama

doctoral thesis

• Title (english): Enediyne compounds in multicomponent reactions
• Author: Mladena Glavaš
• Mentor: Ivanka Jerić (mentor)
• Committee member: Ines Primožič (predsjednik povjerenstva)
• Committee member: Ivica Đilović (član povjerenstva)
• Committee member: Nikola Basarić (član povjerenstva)
• Granter: University of Zagreb; Faculty of Science; (Department of Chemistry); Zagreb
• Defense date and country: 2020-01-29, Croatia
• Scientific / art field, discipline and subdiscipline: NATURAL SCIENCES; Chemistry
• Universal decimal classification (UDC): 54 - Chemistry. Crystallography. Mineralogy

Abstract

Trokomponentna Passerinijeva i četverokomponentna Ugijeva reakcija pripadaju skupini
višekomponentnih reakcija koje uključuju izocijanidnu komponentu. Do sada u literaturi nije
opisana primjena ovih reakcija u sintezi spojeva s endiinskim motivom. Stoga je cilj istraživanja
provedenih u okviru ove doktorske disertacije bio primjena Passerinijeve i Ugijeve reakcije u
sintezi endiinskih peptidomimetika.
Pripravljena su četiri aldehida s različitom duljinom alkilne razmaknice u iskorištenju 78 - 96
%. Dobiveni aldehidi korišteni su u Passerinijevoj i Ugijevoj reakciji te je sintetiziran dvadeset
jedan Passerinijev produkt u iskorištenju 29 - 92 % i trideset dva Ugijeva produkta u
iskorištenju 13 - 93 %. Dokazana je mogućnost postmodifikacija Passerinijevih i Ugijevih
produkata. Pripravljen je jedan postmodificirani Passerinijev produkt u 50%-tnom iskorištenju
te dvadeset pet Sonogashirinih produkata u iskorištenju 34 - 99 %. Ciklizacijom Sonogashirinih
produkata dobiveno je šesnaest makrocikličkih spojeva s endiinskim motivom i esterskom
vezom u iskorištenju 9 - 68 %.

Abstract (english)

Isocyanide-based multicomponent reactions (IMCRs) include a three-component Passerini and
a four-component Ugi reaction. To the best of our knowledge, multicomponent reactions
haven't been utilized in the synthesis of compounds with enediyne motif. Therefore, the aim of
studies carried out within the frame of this doctoral thesis was utilizing Passerini and Ugi
reaction in the synthesis of enediyne peptiodmimetics.
Four aldehydes with different alkyl chains were prepared in 78 - 96 % yield. The aldehydes
were utilizing in the Passerini and Ugi reaction and twenty one Passerini products in 29 - 92 %
yield were prepared along with thirty two Ugi products obtained in 13 - 93 % yield. The
possibility of post-condensation modifications was proved. One post-modificated Passerini
product in 50 % yield and twenty five Sonogashira products in 34 - 99 % yield were prepared.
Cyclisation of Sonogashira products gave sixteen macrocyclic lactones with endiyne motif in 9
- 68 % yield.

• Keywords: endiinski motiv; makrociklički spojevi; Passerinijeva reakcija; Ugijeva reakcija; višekomponentne reakcije
• Keywords (english): enediyne motif; macrocyclic compounds; Passerini reaction; Ugi reaction; multicomponent reactions
• Language: croatian
• URN:NBN: urn:nbn:hr:217:286622
• Study programme: Title: Doctoral study in chemistry; Study programme type: university; Study level: postgraduate; Academic / professional title: doktor/doktorica znanosti, područje prirodnih znanosti, polje kemija (doktor/doktorica znanosti, područje prirodnih znanosti, polje kemija)
• Type of resource: Text
• Extent: 209 str. ; 30 cm
• File origin: Born digital
• Access conditions: Open access
• Created on: 2020-02-06 14:37:19