Student Number : 9201775F -
MSc dissertation -
School of Chemistry -
Faculty of Science / The base/light-induced cyclisation (condensation) reaction between alkyl and carbonyl substituents on biaryl compounds discovered in the University of the Witwatersrand laboratories was used to synthesise benzo[c]carbazoles. Specifically, 5,7-dimethyl-7H-benzo[c]carbazole was synthesised from 2-methyl-1H-indole in 79 % yield over four steps. The reaction sequence involved bromination of 2-methyl-1H-indole at C-3 to give 3-bromo-2-methyl-1H-indole. The subsequent methylation of the amino group to give 3-bromo-1,2-dimethyl-1H-indole was followed by Suzuki coupling with acetophenone-2-boronic acid under non-aqueous reaction conditions to give 1-[2-(1,2-dimethyl-1H-indol-3-yl)phenyl]. Lastly, tBuOK/hν–induced cyclisation of the product yielded the desired benzo[c]carbazole. 10-Methoxy-5,7-dimethyl-7H-benzo[c]carbazole was synthesized analogously in 75% yield from 5-methoxy-2-methyl-1H-indole.
| Identifer | oai:union.ndltd.org:netd.ac.za/oai:union.ndltd.org:wits/oai:wiredspace.wits.ac.za:10539/1785 |
| Date | 16 November 2006 |
| Creators | Nhlapo, Johanna Mepeng |
| Source Sets | South African National ETD Portal |
| Language | English |
| Detected Language | English |
| Type | Thesis |
| Format | 157628 bytes, 1015056 bytes, 201884 bytes, application/pdf, application/pdf, application/pdf, application/pdf, application/pdf, application/pdf |
Page generated in 0.1518 seconds