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Syntheses of novel acyclic amino-amido ligands
Bibliography: page 154.
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| Format: | Thesis |
| Language: | English |
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Department of Chemistry
2015
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| _version_ | 1867613145732743168 |
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| access_status_str | Open Access |
| author | Msimang, Nkosinathi Lorenzo |
| author2 | Elsworth, J F |
| author_browse | Elsworth, J F Msimang, Nkosinathi Lorenzo |
| author_facet | Elsworth, J F Msimang, Nkosinathi Lorenzo |
| author_sort | Msimang, Nkosinathi Lorenzo |
| collection | Thesis |
| description | Bibliography: page 154. |
| format | Thesis |
| id | oai:open.uct.ac.za:11427/16003 |
| institution | University of Cape Town (South Africa) |
| language | eng |
| last_indexed | 2026-06-10T12:31:30.019Z |
| license_str | Not specified — see source repository |
| provenance_str_mv | Harvested via OAI-PMH from UCTD — University of Cape Town Open Access Repository |
| publishDate | 2015 |
| publishDateRange | 2015 |
| publishDateSort | 2015 |
| publisher | Department of Chemistry |
| publisherStr | Department of Chemistry |
| record_format | dspace |
| source_str | UCTD — University of Cape Town Open Access Repository |
| spelling | oai:open.uct.ac.za:11427/16003 Syntheses of novel acyclic amino-amido ligands Msimang, Nkosinathi Lorenzo Elsworth, J F Jackson, Graham Ellis Chemistry Bibliography: page 154. Towards the labelling of biological macromolecules in contrast media, a synthesis of the novel bifunctional amido-ligands N,N' -bis[2-(N'',N''-dimethylamino)ethyl]-4-aminobenzylmalondiamide (67) and the 3-aminopropyl derivative (66) from appropriately C-functionalized malonates by amidation with N,N-dimethylethylenediamine (62) followed by reduction of the respective nitro (64) and cyano (63) groups is described. The synthesis of N,N'-bis[2-(N'',N''-dimethylamino)ethyl]iminodiacetamide (73) from diethyl N-benzyliminodiacetate (79) by amidation· with (62) followed by debenzylation is described. Herein is also reported the unsuccessful attempts to prepare a functionalized pentaamine ligand similar to (73) via the intermediacy of N,N'-bis[2-(N'',N''-dimethylamino)ethyl]-N'''-(2,2-diethoxyethyl) iminodiacetamide (112) whose preparation is also detailed. Attempts to this end via the Mitsunobu and Steglich coupling of N,N' -bis[2-(N'',N''- dimethylamino)ethyl]-N'''-(2-hydroxyethyl)iminodiacetamide (100) with N-tertbutyloxycarbonylglycine (105) also met with failure .. Further failed attempts to secure suitably functionalized intermediates by N-alkylation of diethyl iininodiacetate (70) with appropriate electrophiles are described. The successful functionalization of the pentaamine series of ligands by N-alkylation of (73) withpnitrobenzoyl chloride (118) to give N,N' -bis[2-(N'',N''- dimethylamino)ethyl] N''' -(4-nitrobenzamido)iminodiacetamide (119) is presented. The preparation of the non-functionalized novel trioxo heptaamine ligand N,N' ,N''-tris[2-(N'',N''-dimethylamino)ethyl]nitrilotriacetamide hydrochloride (86a) is also described. An investigative study towards the assembly of a novel triamine system for encapsulating NMR or isotopic NMR-active metal ions for possible use in diagnostic medicine is reported. The key facet to this end is the reported preparation of N,N' ,N''-tris(2-aminoethyl)propane-1,2,3-tricarboxamide (89) by controlled amidation of trimethyl propane 1,2,3-tricarboxylate (88) with ethylenediamine. The syntheses of functionalized and non-functionalized novel tetraamine dioxo and trioxo ligands from glycine, ethyl N-benzylglycinate (78), L-valine, and L-lysine via classical peptide synthesis methodology (in part) are described. 2015-12-28T06:11:05Z 2015-12-28T06:11:05Z 1990 Master Thesis Masters MSc http://hdl.handle.net/11427/16003 eng application/pdf Department of Chemistry Faculty of Science University of Cape Town |
| spellingShingle | Chemistry Msimang, Nkosinathi Lorenzo Syntheses of novel acyclic amino-amido ligands |
| thesis_degree_str | Master's |
| title | Syntheses of novel acyclic amino-amido ligands |
| title_full | Syntheses of novel acyclic amino-amido ligands |
| title_fullStr | Syntheses of novel acyclic amino-amido ligands |
| title_full_unstemmed | Syntheses of novel acyclic amino-amido ligands |
| title_short | Syntheses of novel acyclic amino-amido ligands |
| title_sort | syntheses of novel acyclic amino amido ligands |
| topic | Chemistry |
| url | http://hdl.handle.net/11427/16003 |
| work_keys_str_mv | AT msimangnkosinathilorenzo synthesesofnovelacyclicaminoamidoligands |