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The synthesis of biologically active core structures such as indoles, imidazoles and pyrrolo-[2,1-j]quinolines can be achieved using known methodologies including electrophilic cyclization and the Larock indole synthesis. The Larock indole synthesis was performed in order to create a pyrrolophenanthridinone core structure through the annulation of alkynes. Initial investigations into the synthesis of pyrrolophenanthridinone afforded pure compounds in lower yields than other previously published methodologies. Pyrrolo-[2,1-j]quinoline derivatives were formed in high yields using electrophilic cyclization and subsequent palladium-catalyzed cross coupling reactions such as Suzuki and Sonogashira coupling, which were employed to form biologically active analogues. Functionalization of a pyrrolo-[2,1-j]quinoline core using Sonogashira coupling failed while Suzuki coupling has proven to be effective. Attempts to synthesize bicyclic derivatives of imidazole core structures, such as thiophene-fused imidazoles, using electrophilic cyclization were unsuccessful.
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Sidman, Eli, "The Synthesis of Biologically Active Core Structures Using Electrophilic Cyclization and Palladium-Catalyzed Annulation" (2012). Senior Projects Spring 2012. 86.
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