Synthesis Of Pyrroloquinolines Based On The Tandem Reactions Of Methyl Isocyanide

There are many heterocyclic compounds over the world, accounting for about half of species of organic ones. The diversity synthesis of nitrogen-containing heterocyclic compounds has been one of the concerned aeries of organic chemistry, because of their extensive bioactivities. Of all the numerous heterocyclic compounds, the pyrrolo[2,3-c]quinoline is a structural motif among natural products, which is founded that some alkaloids containing this structure exist in marine living beings. These compounds possess various bioactivities, such as antibacterial, antifungal and antimalarial activities, as well as the ability against several cancer cells. However, there are only a few researches reported concerning the synthesis of these compounds. In addition, the synthetic strategies involved mostly taking 3-phenylpyrrole as the substrate, which could be applied to construct the pyridine ring to complete the pyrrolo[2,3-c]quinoline system. Therefore, the development of a novel strategy for the divergent syntheses of pyrrolo[2,3-c]quinoline alkaloids is of major importance.In this thesis, we develop the tandem bicyclization of methyl isocyanides with readily available iminochalcones, which provides a new synthesis strategy to generate a series of polyfunctionalized pyrrolo[2,3-c]quinoline alkaloids. In this reaction, two rings, pyrrole and pyridine rings, are formed simultaneously in one step, which represent an original strategy. Meanwhile, this method has the advantages of mild conditions, broad range of substrates, oxidized by atmosphere together with high yield and so on. The structures of pyrrolo[2,3-c]quinoline compounds achieved are confirmed by ¹H NMR,¹³C NMR, and HRMS?ESI?.