Studies on Transition Metal Catalyzed Synthesis of 5 Membered Heterocyclic Compounds

Abstract

Frequently found in natural products and pharmaceuticals, pentacyclic heterocyclic compounds exhibit a variety of biological activities and have wide applications in synthetic, medicinal and polymer chemistry. The nucleophilic reaction of olefins with transition metals as catalysts is a powerful method for the efficient atomistic and stepwise economical construction of various heterocyclic compounds. In addition, it is highly desirable to develop a mild and efficient technique to construct carbon heteroatom bonds, which has long been considered through the functionalization of C H bonds. Therefore, the development of novel organic syntheses of these heterocyclic compounds with high efficiency, high selectivity, high utilization and environmental friendliness remains a challenging research issue. In this thesis, the following subjects are covered. 1) Pd( catalyzed regioselective intramolecular C H amination of 1,1 disubstituted alkenylamines, 2) Ag catalyzed simple tandem olefin isomerisation/intramolecular hydrogenation of alkenylamines with various allylic tethers, and 3) Cu( catalyzed synthesis of 1 disubstituted isoindolines via 1,4 diamination reaction of dienes. The above topics suggest new and efficient synthetic methods of benzoxazolines, benzoxazoles, and isoindolines, which are bioactive, natural products, pharmaceuticals, and functional heterocyclic compounds.