Synthesis And Spectrum Analysis Of N-Ssubstituted Indole Derivatives

Indole derivatives is a very important class of organic raw materials and chemical products. The compounds containing indole ring are widespread in nature, which occupy a large proportion of the known natural products. Usually, most of these compounds have significant property due to its particular chemical structure, and have an important role in agriculture, industry, medicine, etc. Based on the understanding about the application of indole derivatives, many synthetic methodologies of indole derivatives have been reported.In this dissertation, we also gave a brief summary about it.In this dissertation, series of N-substituted indole derivatives were designed and synthesized mainly based on the nucleophilic substitution reaction of indole ring. Through 1D and 2D NMR techniques,1H and 13C NMR signals of different N-substituted indole derivatives were assigned.The relevant spectrums were compared and some conclutions were drawn from it. For example, the chemical shifts of protons and carbons in the indole ring of N-substituted 3-methyl indole derivatives and 5-benzyloxy indole derivatives are higher than the corresponding N-substituted Indole ring derivatives not substituted, which may be due to the electronic substituent effects. The fragmentation pathway of mass spectra of these compounds were studied and summarized according to Electrospray Ionization Mass Spectrometry(ESI-MS).We find that the C-N and S-N bonds are easy to break in the mass spectrometric, which may be due to the relative stability of the indole ring itself. The molecular structure can be identified from fragment ion of compounds in electrospray ionization mass spectrometer. All the conclutions can be used as references to other analogues. Finally, all the compounds were studied by the infrared absorption spectrum.