Study On Cascade Reaction Of 3-Methyleneoxindole

Indole is a privileged framework occurring natural product and pharmaceutical compound,which attracted synthetic interest for organic and medicinal chemists.3-Methyleneoxindole is easily ready from isatin and have high react activity,which usually as substrate for the synthesis of spirooxindoline.In this thesis,we have successfully developed some methods for the synthesis of indole-fused hetecyclic compounds starting from 3-methyleneoxindole,and some results were obtained as follows.Under the combined catalysis of Cu?OTf?₂/HOTf,the domino annulation reaction of o-arylalkynyl acetophenones with 3-phenacylideneoxindoles in refluxing 1,2-dichloroethane selectively afforded functionalized spiro[indoline-3,7'-tetrapheno[7,6-bc]furans]and spiro[indeno[1,2-b]naphtho[2,1-d]furan-7,3'-indolines]have been developed.The forming of two kinds of compound depend on electron effect of the substituents on both substrates.All the new products were characterized by IR,¹H NMR,¹³C NMR and HRMS spectroscopy.The single structure of three compounds were determined by X-ray diffiraction method.The convenient simple proctocol for the construction of tetrahydrospiro[carbazole-1,3'-indoline]s and polysubstituted 3-?9H-carbazol-2-yl?indolin-2-ones have been developed by using indole,ketone and 3-methyleneoxindole as substrate and TfOH as catalyst.The tetrahydrospiro[carbazole-1,3'-indoline]s were formed when the reaction carried out in one-pot two-step.3-?9H-carbazol-2-yl?indolin-2-ones were obtained while the reaction performed in one-pot under similar condition.The two kinds of reaction displayed the molecular diversity of multiple-component reaction.All the new compounds were characterized by IR,¹H NMR,¹³C NMR and HRMS spectroscopy.The single structure of eighteen compounds were determined by X-ray diffiraction method.The cascade/Diels-Alder reaction for the construction of spiro[cyclohexane-1,3'-indolines]in good yield and high diastereoselective by using pinnacol and its derivertives and 3-methyleneoxindoles as substrate and Br???nsted acid HOAc as catalyst and B[mim]Br as solvent have been developed.All the new compounds were characterized by IR,¹H NMR,¹³C NMR and HRMS spectroscopy.The single structure of two compounds were determined by X-ray diffiraction method.