Ready Access to Carbazole and Carboline Functionality
Date
2020
Authors
Gin, Emma
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This thesis consists of two scientific articles and is preceded by an overview that contextualises the published work.
The first part of this thesis is comprised of Publication 1 and its corresponding supporting information. It is concerned with the synthesis of compounds 2-arylcyclohex-2-en-1-one with various R substitutions utilising the Pd-catalysed Ullmann cross-coupling. Subjecting these compounds to a reductive cyclisation followed by aromatisation generates carbazoles with various substitution patterns. This methodology was also used to generate natural products 3-Methyl-9H-carbazole, Glycoborine, Glycozoline, Clauszoline K, Mukonine, and Karapinchamine A.
The second part of the thesis is comprised of Publication 2 and its corresponding supporting information that builds upon the above-mentioned publication, where we were able to generate a 2-nitropyridine; 2-(2-Nitropyridin-3-yl)-cyclohex-2-en-1-one. Subjecting this compound to a reductive cyclisation followed by aromatisation generates alpha-carboline. The aforementioned 2-nitropyridine as its various N-regioisomers were also synthesised allowing access to to beta-, gamma-, and delta-carbolines. This methodology was also used to generate natural product, beta-carboline containing harman.
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Thesis (MPhil)
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