The synthesis of Benzo[C]carbazoles

Show simple item record Nhlapo, Johanna Mepeng 2006-11-16T09:43:16Z 2006-11-16T09:43:16Z 2006-11-16T09:43:16Z
dc.description Student Number : 9201775F - MSc dissertation - School of Chemistry - Faculty of Science en
dc.description.abstract 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. en
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dc.format.mimetype application/pdf
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dc.language.iso en en
dc.subject Suzuki Coupling en
dc.subject potassium t-butoxide en
dc.subject indole en
dc.title The synthesis of Benzo[C]carbazoles en
dc.type Thesis en

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