Hansen, Birgitte Bork (2016) Stability studies of isotope-labelled carboxamides and a palladium-catalysed carbonylative approach using imines to form 4-quinolones. Master Thesis, N/A (N/A). 0-0. ISSN N/A

Abstract

Transition metal chemistry is an important and expanding field for the construction of carbon-carbon and carbon-heteroatom bonds. Applying the two-chamber system and the CO-surrogate, COgen, to palladium-catalysed carbonylative reactions, enables the insertion of the carbonyl functionality into various different molecules in a safe and controllable way.
This thesis describes the theory and work of two different projects. After an introduction to catalysis with palladium in chapter 1, the first project, done in collaboration with Novartis, is described in chapter 2. The chapter deals with stability-studies of molecules labelled with 18O on carboxamides, which is a highly present functionality in many pharmaceuticals. Isotope-labelling this linkage with 13C and 18O, possibly with 13C18Ogen, would gain M+3 compounds. If this label proves stable and does not back-exchange with 16O in an aqueous environment, these stable isotope-labelled compounds can be applied as internal standards for the precise quantification of analyte in a sample using mass spectrometry.
Chapter 3 describes the second project, which deals with the synthesis of the 4-quinolone structure, a core-structure found in many anti-bacterial drugs as well as in natural compounds. The project has dealt with the synthesis of the structure using a palladium-catalysed carbonylative approach from imine-structures, fol-lowed by an intramolecular nucleophilic aromatic substitution reaction.

Item Type:	Article
Keywords:	N/A
Date Deposited:	04 Jan 2017 00:45
Last Modified:	04 Jan 2017 00:45
URI:	https://oak.novartis.com/id/eprint/30134