Synthesis of nitrogen, oxygen, sulfur and selenium containing five-membered heterocycles

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Five-membered heterocyclic motifs having O, N, S and Se atoms are previlaged structural scaffolds due to their interesting biological and medicinal properties. The development of simple and efficient synthetic methods for their construction is thus important in synthetic chemistry. The thesis has six chapters. The first chapter describes the synthesis of oxazolidines via an intramolecular C(sp3)-H alkoxylation of N-methyl amino alcohol. In the second chapter, the synthesis of substituted imidazolidines is presented via an intramolecular C(sp3)-H alkylamination of N-methyl 1,2-diamines. The third chapter focuses on domino ring opening and oxidative cyclization of styrene oxides with N-methylanilines. In the fourth chapter, Al(salen)Cl-catalyzed cycloaddition of optically active aziridines with isoselenocyanates is discussed. The fifth chapter deals with BF2OTf∙Et2O-catalyzed cycloaddition of thiirane with isothiocyanates, isoselenocyanates and carbodiimides. The sixth chapter is focused on the Pd-catalyzed ortho-alkylation of amides with epoxides.
Supervisor: Tharmalingam Punniyamurthy