Effective Synthesis Of Fused Indole And Isoquinoline Derivatives

The thesis made up of four parts.The first section showed the significance and base of the selection of the subject, the original points and the research methods, the research progress of tandem reactions for the synthesis of fused indole and imidazole compounds home and abroad.The second section developed a formal method of [3+3] heterocyclization of enaminones for forming tetracyclic indolo[2,3-b]quinolines. Under microwave irradiation, 3-aroylidene-2-oxindoles and N-arylenaminones as starting materials, using EtONa as a base and ethanol as a solvent, providing a high yield one-pot synthesis of a series of indolo[2,3-b] quinolines derivatives. The reaction underwent the Michael addition reaction, tautomerism and intramolecular cyclization process, which constructed potentially biological active indolo[2,3-b]quinoline skeleton in one-step manner.The third section investigateed the domino reaction between 3-aroylidene-2-oxindo-les and arylhydrazines. A series of potentially biological active pyridazino[3,4-b]indole derivatives were synthesized in ethanol through microwave-assisted reaction of 1,3-dicarbonyls and hydrazine using potassium carbonate as a base catalyst. The reactions have many features including simple operation, high efficiency, and short reaction period.The fourth section developed Pd/Cu co-catalyzed reactions of polysubstituted imidazoles and arylacetylenes under an argon conditions. These reactions in anhydrous DMF smoothly proceeded to new imidazo[2,1-a]isoquinolines via Sonogashira coupling and intramolecular cyclzation process.All the structures of the products were determined by 1H NMR, IR and HRMS. Furthermore, the structures of some products were confirmed by X-ray analysis. The microwave-assisted reactions mentioned above have advantages of simple conditions, short reaction periods, easy work-up, straight forwardness of the procedure.