Study On Selective Alkylation Of Polysubstituted Indoles

Indole is widely existed in drug molecules and natural products,and is one of the most common nitrogenous heterocyclic compounds.Indole and its derivatives have unique biological and pharmaceutical activities.In 1886,Baeyer firstly realized the chemical synthesis of indoles.Since then,the preparation of indole rings and its further functionalization have attracted more attentions of organic chemists.This thesis focused on the alkylation of polysubstituted indoles,which have been used as raw materials for the study of multisubstituted indoles.1、The chiral phosphoric acid catalyzed N-alkylation of indoles was established with high diastereoselectivity and high enantioselective.Additionally,many alkaloids based on the indoles could be modified through this transformation,and the N,O-acyclic aminals could be used as organic synthesis intermediates of natural products.2、Pyrrole [1,2-α] indoles were synthesized from 2-methyl-indoles and ethyl trifluoropyruvate in a one-pot cascade reaction with environmentally friendly iron as catalyst and tetramethyl-guanidine as organic base,which were widely existed in bioactive natural products.This transformation was efficient under mild condition using environment-friendly metal with good regioselectivity.