Regional-selective C-C Bond Formation Of N Protected Indoles Induced By Trimethyl Bromosilane

Indole is a very common core structure in the chemical molecular skeleton of heterocycles,they are applied in medicines,natural products,agricultural chemicals,spices,dyes and functional materials,and other fields have a wide range of applications,the synthesis of them are brings hope for human life and health.Indole and it’s derivatives have high biological activity and pharmacokinetics,among which the natural biindole alkaloids and the synthetic biindole compounds have anticancer activity.Biindole,as a pharmacodynamic molecule with a wide range of functions,is one of the heterocyclic compounds widely existing in natural and synthetic biologically active compounds.However,with the improvement of the national economy,the problem of environmental pollution caused by chemicals can not be ignored.Therefore,in order to improve the quality of human living environment,we as the main practitioners of the chemical industry,have the obligation to reduce the emissions of pollutants and toxic substances in the process of chemical synthesis,and reduce the generation of by-products at the same time.It is urgent to find and develop a green synthesis method.The main research content of this paper will be explained from the following two aspects:The first chapter is the literature review.Firstly,the application and significance of indole and its derivatives in daily life are described.Then,the application and research progress of dimerization of indole to form 2,2’-bisindole and 3,3’-bisindole are described.Finally,the research progress and application of 2,3’-diindole in recent years are introduced.In the second chapter of this paper,C-C bond was successfully constructed by using5-chlorine-N-methyl indole as substrate,potassium phosphate trihydrate as base,trimethyl bromosilane as additive,dichloromethane and chloroform as solvent by reacting at room temperature for 12 hours.1,1’-dimethyl-2,3-dihydrogen-2,3’-indole derivatives were successfully constructed by N-H-protected indole regional-selectivity.Then,under the optimal conditions,the universality of the substrate was explored in this paper.It was found that in the reaction process,the substitution group of N-methyl indole as the electron-donating group was better than the electron-withdrawing group,and the gram-scale experiment was done.Finally,the possible reaction mechanism was proposed through the control experiment.In the third chapter,N-methylindole was used as the substrate and dimethyl sulfoxide was used as the sulfur source,methylthiolation takes place at the 3-position of indole.The fourth chapter of this paper is the summary and prospect.Through the summary of the whole process of the experiment,it is found that although the synthesis method of this paper is simple,the yield of indole derivatives obtained by the reaction is high,and20 compounds are synthesized,There still exist some shortcomings,which need to be further improved.