Study On New Method For The Synthesis Of The Pyrrolo [2,3-c]Quinoline Alkaloid Analogues

The azomethine ylides generated from azomethine imines can react with the electron-deficient alkenes or alkynes via the 1,3-dipolar cycloaddition reaction. Among them, the [3+2] cycloaddition of azomethine ylides and olefins has become one of the most effective method for the stereoselective synthesis of tetrahydropyrrole derivatives, and this method also has been used in the synthesis of natural products.While, the research about using one pot tandem reaction of azomethine ylides to build multiple ring system is rarely reported.In this thesis, we systematically studied the bicyclization of various azomethine imines and o-imino chalcones. The high steroselective hexahydropyrrolo[2,3-c]quinolines are generated from the bicyclization of a-cyano azomethine imines and imino chalcones under metal- and ligand-free conditions, subsequently, decyanation and oxidative aromatization occur to provide pyrrolo[2,3-c]quinoline derivatives. And the natural products such as marinoquinolines A-F contain this pyrrolo[2,3-c]quinoline motif. Therefore, three bonds and two rings are generated in this "one pot" reaction, and this strategy provides a simple and efficient method for the divergent synthesis of pyrrolo[2,3-c]quinoline alkaloids.