Synthesis Of Novel Indole Compounds-synthesis Of Carboline Sulfonamide And 3,3-Disubstituted Oxindoles

2,3-benzopyrrole(indole)is an aromatic heterocyclic organic compound.Indole alkaloids are widely existed in nature and have strong biological activities.Therefore,indole compounds have important application prospects in organic synthesis.In this paper,the synthesis of carboline sulfonamide and oxyindoles derivatives with indolepyrrole ring is described respectively:The first part is synthesis of carboline sulfonamide.A convenient synthesis of carboline sulfonamide was achieved via sulfonamidation under alkaline conditions.The reactions between?-or?-carbolines and N-fluorobenzenesulfonamide(NFSI)were investigated in the presence of Na H.?-and?-carboline sulfonamide derivatives were obtained in good yields.These reactions provide a new pathway for carbline sulfonamide derivatives.Four?-carboline sulfonamide derivatives and one?-carboline sulfonamide derivative were synthesized by this reaction,and their structures were characterized by ¹H NMR,¹³C NMR,IR and HRMS.the structure of typical compound"?-carboline sulfonamide"was determined by X-ray single crystal diffraction,and the structure of"?-carboline sulfonamide"and"?-carboline sulfonamide"was determined by remote ¹H-¹³C heteronuclear multi-quantum correlation(HMBC)and heteronuclear single quantum correlation(HSQC).We speculated that the reaction mechanism was that N-S bond of N-fluorobenzenesulfonamide was broken to provide benzenesulfonyl group under the influence of the reaction intermediate carboline nitrogen anion.This is a new application of commercialized reagent N-fluorobenzenesulfonamide as electrophilic fluorination,free radical fluorination and amination reagent.The second part is the synthesis of antimony oxide derivatives oxyindoles derivatives 3-phenacylideneoxindoles is usually synthesized by isatin and substituted acetophenone through condensation and dehydration,3-phenacylideneoxindoles which contain the structure of?,?-unsaturated ketones,play an important role in rapid construction of 3,3-substituted oxindoles as Michael acceptors.An efficient K₂CO₃catalyzed conjugate Michael addition of nitroalkanes to 3-phenacylideneoxindoles has been developed,providing series of novel 3,3-disubstituted oxindoles in good yields(60-89%)and The reaction had a high degree of regional selectivity within a few minutes.the product had good diastereomeric selectivity after methanol recrystallization(dr 1:4-1:10).Fourteen novel indole derivatives were synthesized,which not only contain multiple functional groups,but also have 2-3 chiral centers.The NOE spectrum shows that this type of reaction is characterized by the configuration of syn/syn.The structure of the compound was characterized by ¹H NMR,¹³C NMR,IR and HRMS.