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Title: Studies on solid phase organic chemistry for combinatorial synthesis
Author: Arumugam, V.
Awarding Body: University of Cambridge
Current Institution: University of Cambridge
Date of Award: 1999
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This thesis details the study of solid phase palladium mediated (Heck reaction) chemistry for the synthesis of acyclic and cyclic products. Initially, a few Heck reactions were optimised in solution phase to study the effects of aromatic substituents, before attempting similar reactions on solid phase. Initial Heck reaction studies were carried out on Wang resin to which a template (3-iodo-4-nitrophenol) was attached via an ester linkage. The Heck reactions worked well on solid phase and the products were cleaved from the resin as carboxylic acids by acidolysis. When reduction of the nitro group was carried out on the Wang resin bound template, it was observed that the by-products of reduction caused premature cleavage of the ester linkage. Therefore, an alternative resin, MBHA (4-methyl benzhydrylamine) Rink amide resin was used. Following the intermolecular Heck reactions, intramolecular Heck reactions were attempted to solid phase, and indole and oxindole derivatives were successfully synthesised. The syntheses of benzothiazole analogues were carried out using a nickel (0) catalyst since the reaction with palladium (0) resulted in poor yields. The products were cleaved from the resin as carboxamides and the purity was detected by HPLC (High Performance Liquid Chromatography) linked to an ELSD (Evaporative Light Scattering Detector). As part of the project, a variety of analytical techniques such as elemental analysis, FTIR (Fourier Transform Infrared) spectroscopy, gel phase 13C-NMR (Nuclear Magnetic Resonance) spectroscopy, and MS (Mass spectrometry) were studied for the purpose of compound characterisation and reaction monitoring on solid phase.
Supervisor: Not available Sponsor: Not available
Qualification Name: Thesis (Ph.D.) Qualification Level: Doctoral
EThOS ID:  DOI: Not available