Studies on site-selective functionalization of N-heterocycles

Abstract

Nitrogen-containing heterocycles are the most abundant core scaffolds found in a myriad of bioactive compounds. In this regard, the development of site-selective functionalization of nitrogen-containing cyclic compounds is important in that this methodology has provided the efficient and straightforward synthetic route to effectively preparing the diverse classes of valuable compounds. This dissertation describes the Ir(III)-catalyzed site-selective C-H amidation of indole substrates using organic azides as a nitrogen source. Also, the important factors controlling site-selectivity are examined with the understanding of reaction mechanism using computational and statistical methods. In addition to method in diversifying the functional groups of the N-heterocycles, the method for structural diversification of saturated cyclic amine compounds using difluorocarbene has been developed.