Design And Synthesis Of Novel1H-(1,2)Diazepino(4,5,6-cd) Indol-6(5H)-ones

Indole moieties are widely existed in numerous bioactive compounds and nature products, thus potential bioactive compounds containing indole cores attracts continuous attentions in both organic synthesis and drug discovery. As one of the indole-derived heterocycles, substituted1H-(1,2) diazepino (4,5,6-cd) indol-6(5H)-ones show good pharmacological activities, namely anti-cancer, anti-malaria, CHK1inhibitation and anti-virus et al.The thesis focuses on the synthesis of3-aryl-lH-(1,2) diazepino (4,5,6-cd) indol-6(5H)-ones and its derivatives. By optimizing the process of substituted indoles synthesis,3-acylation of substituted indole and cyclization with hydrazine under acidic conditions, the target compounds with different substituted aryl group were obtained.The thesis divides into three parts:Firstly, exploring the synthetic route of4-methyl-6-fluoro-1-indoline from5-fluoro-2-methyl-3-nitrobenzoic acid. Secondly,the synthesis of substituted benzoic acids with m/p-Br, CH2Br, CH2N3-aryl,-N-Cbz-3-pyrrolidine,-N-Cbz-3-methyl-pyrrolidine, etc..Lastly, summarizing the general method for these compounds through synthesis of3-aryl-lH-(1,2) diazepino (4,5,6-cd) indol-6(5H)-ones (e.g.:m/p-Br, p-CH2Br, m/p-CH2N3-aryl). applying the general methods for the synthesis of several complicated3-aryl-1H-(1,2) diazepino (4,5,6-cd) indol-6(5H)-ones.The final products were characterized with1H NMR,13C NMR and Mass spectrum.