4 - Amino-indole And Its Derivatives

The indoles is an important kind of intermediate in industry of fine chemicals,which is widely used in medicine,pesticide,spicery,food and feed additive,dye and many other fields. Research of its application has never stoped,and its new application is exploited continually. In this dissertation,the synthetic methods of 4-aminoindole and its derivatives were studied, practical and feasible ways were designed and the mechanisms of important reactions were discussed as well.Firstly,2,6-dinitrotoluene condense with N,N-dimethylformamide dimethyl acetal at 105℃to prepare 2,6-dinitro-β-(dimethylamino)styrene.And then 2,6-dinitro-β-(dimethylamino) styrene react with semicarbazide hydrochloride to obtain(2,6-Dinitrotrophenyl)acetaldehyde semicarbazone,At last,(2,6-Dinitrotrophenyl)acetaldehyde semicarbazone was reduced to prepare 4-aminoindole.Its three derivatives(4-acetamidoindole,4-azidoindole, 4-(1-piperazinyl)indole) were also synthesized.The structure of the synthetic products were characterized by infrared(IR),mass spectra(MS) and ~1H nuclear magnetic resonance(NMR).It proved that the synthetic method was feasible and each intermediate and the target product conformed to the design requirements.It was prognosticated that the way using the original raw material (2,6-dinitrotoluene) to prepare 4-aminoindole and its deraletives was novel,practical and effective.