Study On The Synthesis Of Indoline Compounds Without Metal Mediation

Indolines play an important role in both synthetic chemistry and pharmaceutical chemistry.Indolines and their derivatives exist widely in nature and are important structural units and components of natural products,drug intermediates,biological inhibitors,organic dyes,and even organic photoelectric materials.It is worth exploring to construct indolines by a green,efficient and mild synthesis strategy.In this paper,the cyclization reaction involving o-azide benzaldehyde without metal mediation is mainly concerned.The details are as follows:1.In this paper,indolin-3-one was synthesized from o-azide benzaldehyde and phenylacetylene with the mediation of base.In this method,dimethyl sulfoxide was used as solvent and oxidant,tetrabutylammonium hydroxide aqueous solution as base,and the reaction conditions were mild at room temperature.Twenty-four 2-benzylindolin-3-one derivatives were obtained with moderate to excellent yield,with the highest yield of 90%.The structures of the target compounds were characterized and analyzed by ¹H NMR and ¹³C NMR.Through control experiment and literature research,the reaction mechanism was explored.The derivatization experiments of indolin-3-one were carried out,and two derivatives were obtained with medium to excellent yields,which proved the practicability of the reaction system.2.This paper presented a metal-free catalyst for the formation of 2-cyanoindoline compounds from o-azobenzaldehyde and acetonitrile.Acetonitrile was used as solvent and synthon at the same time,the reaction condition was mild and the reaction was rapid.The highest yield of twelve target compounds reached 97%.The formation of the target compound can be completed in 10 minutes.The structures of all the target compounds were characterized by ¹H NMR and ¹³C NMR.Through control experiment and literature research,the reaction mechanism was explored.