Ready Access to Carbazole and Carboline Functionality

Abstract

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.