Study On The Tandem Reaction Of Organic Azides And Its Application In The Synthesis Of Quindoline

Organic azides are important class of synthons with good reactivity in organic synthesis.The most typical ones is that the organic azides could provide three nitrogen atoms to undergo cycloadditon reaction with an unsaturated compounds(such as olefins or alkynes)to form 1,2,3-triazoles.At the same time,the organic azides could also provide one nitrogen atom by removing one molecule of nitrogen to form other nitrogen heterocycle compounds,such as hydrazines,imidazoles,quinolines.However,for some special functional quinolines have not been reported.In particular,the 3-position substituted(such as nitro-)quinoline has strong biological activity,including anti-cancer,anti-malarial,anti-asthma,anti-diabetic,antibacterial,anti-tumor.Moreover,the substituted quinolines containing nitrogen atom at 3-position are precalent in nature products and a wide range of biological active compounds.Their syntheses have been widely concerned.In this paper,the bifunctionalized 2-azidobenzaldehyde was used as a synthon to reacted with the nitro-olefin under the catalyst of Cu(I)to synthesize a series of 3-nitroqunoline compounds.The solvent-free reaction conditions eliminated the formation of some byproducts and improved the efficiency of the reaction.This method has high yields,easy availability of raw materials,convenient operation,and the by-products only nitrogen and water,which provides a new strategy for the synthesis of 3-position nitrogen-containing quinoline.Moreover,with these 3-nitroquinoline compounds,this paper also realized the total synthesis of quindoline and its derivatives in only three steps.Compared with the existing literature,the reaction conditions are mild,the steps are short,the yield is high,and no precious metal is used,which has a strong application value.