Synthesis Of Some Nitrogen-containing Compound

Nitrogen-containing compounds exist widely and have a series of important functions and applications that cannot be ignored.Among them,polycyclic indoles,as a class of nitrogen-containing compounds with unique skeleton,are widely used in medicine,synthetic chemistry,organic photoelectric materials and other fields.As an important class of polycyclic indole compounds,the synthesis of 10H-indole[1,2-a]indole has attracted extensive attention.At present,a variety of synthesis methods of10H-indole[1,2-a]indole derivatives have been reported,but most of these synthesis methods require preparation of complex precursors,use of noble metal catalyst or high reaction temperature.These reaction requirements limit the convenient synthesis of10H-indole[1,2-a]indole derivatives.Therefore,the development of a simple and general synthesis method of 10H-indole[1,2-a]indole derivatives is a worthy research topic.In addition,as a kind of basic and widely used nitrogen-containing compounds,the synthesis of azo compounds also attracts attention.Based on this,we developed two synthesis methods of 10H-indole[1,2-a]indole derivatives and a novel preparation method of azo compounds.Part one: A synthesis method of polycyclic 3,3’-biindole compounds using silver trifluoromesylate as catalyst and indole and indole derivatives as raw materials was developed.In this reaction,the polycyclic 3,3’-biindole skeleton structure is rapidly constructed through nucleophilic addition and ring isomerization catalyzed by silver trifluoromethanesulfonate.Polycyclic 3,3’-biindole compounds were transformed into polycyclic 2-indolone derivatives by Selectfluor as oxidant.This method provides a new strategy for the synthesis of polycyclic 3,3’-biindole compounds and their derivatives.Part two: A synthesis method of 10H-indole[1,2-a]indole derivatives was developed using indole derivatives,o-iodobenzaldehyde and dimalonate as raw materials,iodine as catalyst,zinc iodide as cocatalyst,through the process of intramolecular cycloaddition and hydrogen migration.a variety of 10H-indole[1,2-a]indole derivatives were synthesized by this method.The method has the advantages of simple operation and mild reaction condition.Part three: A method for the synthesis of azo compounds using Selectfluor as oxidant was established.A variety of azo compounds were synthesized by dehydrogenation and oxidation of hydrazine compounds at room temperature,in air and without metal.In addition,the synthesized azo compounds can be converted to n-acetylaniline and 1,2-stilbene under the action of blue light,which preliminarily verifies the potential application of this oxidation reaction in synthetic chemistry.