• norsk
    • English
  • English 
    • norsk
    • English
  • Login
View Item 
  •   Home
  • Faculty of Mathematics and Natural Sciences
  • Department of Chemistry
  • Department of Chemistry
  • View Item
  •   Home
  • Faculty of Mathematics and Natural Sciences
  • Department of Chemistry
  • Department of Chemistry
  • View Item
JavaScript is disabled for your browser. Some features of this site may not work without it.

Development of Methodology for the Synthesis of Cytotoxic NHC-Ag-Complexes

Kringlen, Hilde Dalshov
Master thesis
Thumbnail
View/Open
144815384.pdf (2.861Mb)
URI
https://hdl.handle.net/1956/12624
Date
2016-06-02
Metadata
Show full item record
Collections
  • Department of Chemistry [345]
Abstract
Recently disclosed silver N-heterocyclic carbene complexes holding 4-alkylated imidazoles have been proved to hold cytotoxic properties. In this work, derivatives of such alkylated imidazoles were synthesised to be complexed with silver(I). N,N-diphenyl-4-methylimidazolium teterafluoroborate was synthesised by means of a two step synthetic pathway. The synthesis involved a selective N1-arylation of 4-methyl-1H- imidazole using the palladium-catalysed Buchwald N-arylation method, followed by a direct quaternisation using phenylboronic acid. A 2^2 factorial design was initiated to investigate how the reaction temperature and reaction time influenced the conversion of the starting material. No clear correlation was found, and a full conversion of the starting material was not obtained. The formation of the product was confirmed by LC-MS, but a successful isolation was not achieved. A N,N-diphenyl-4-heptylimidazolium tetrafluoroborate synthesis was attempted by means of a seven/eight step synthetic pathway. The synthesis involved a selective iodination of an imidazole backbone, followed by an altering of the electronic properties by the introduction of an auxiliary group. A first attempt of implementing this step using flow chemistry was successfully performed. The backbone iodide was replaced in a Sonogashira coupling reaction, in which the installed alkyne moiety was reduced using gaseous hydrogen in the presence of Pearlman's catalyst. An attempt of reducing the alkyne moiety using indium as the reducing agent was carried out, without furnishing the desired product. The palladium-catalysed Buchwald method was used to perform an N1-arylation, before phenylboronic acid was utilised in an attempt to obtain the quaternised imidazole. Only traces of the desired product were observed. It is thought that the imidazole side chain constitutes a steric hindrance that reduces the conversion of the starting material.
Publisher
The University of Bergen
Copyright
Copyright the Author. All rights reserved

Contact Us | Send Feedback

Privacy policy
DSpace software copyright © 2002-2019  DuraSpace

Service from  Unit
 

 

Browse

ArchiveCommunities & CollectionsBy Issue DateAuthorsTitlesSubjectsDocument TypesJournalsThis CollectionBy Issue DateAuthorsTitlesSubjectsDocument TypesJournals

My Account

Login

Statistics

View Usage Statistics

Contact Us | Send Feedback

Privacy policy
DSpace software copyright © 2002-2019  DuraSpace

Service from  Unit