| Summary: | In this thesis the development of novel synthetic methodologies and their application towards the syntheses of cell cycle regulators using palladium-catalysed cross-coupling reactions and microwave assisted organic synthesis is presented. This synthetic methodology was developed in order to generate small libraries of nitrogen containing heterocycles with inherent structural diversity. To achieve this aim, a palladium catalysed cross-coupling approach was chosen, in which, particularly, carbon-carbon and carbon-nitrogen bond forming reactions were implemented. For palladium catalysed C-C and C-N bond forming reactions, microwave-assisted procedures can improve the combinatorial productivity significantly and, consequently, in this work microwave conditions were systematically implemented to minimise the reaction times, optimise chemical yields, and reduce solvent waste, which is in concurrence with the growing societal need for sustainable developments. A general and versatile method for the synthesis of β-aryl/alkylarylidene malonates has been developed. It has been shown that the key step involves the coupling of an arylboronic acid with a β-chloroalkyl/arylidene malonate, in the presence of K<sub>2</sub>CO<sub>3</sub> and 1 mol% of the air-stable palladium catalyst (POPd) under microwave irradiation, to afford β-aryl/alkylarylidene malonates in good yields. The combination of mild reaction conditions, an air-stable catalyst, and microwave assisted chemistry, and high levels of functional group compatibility render this an attractive synthetic approach to this class of compounds. Furthermore, herein is reported a novel method for the synthesis of <i>N</i>-substituted oxindoles.
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