Synthesis Of Novel Spiro Oxyindole Compounds

The structrue of spirooxindole,widely found in natrual products and bioactive compouds,was characterized by the oxindlole ring coupled with different spiro ring,at the C3 position.Spirooxindoles had been found to show a wide range of biological activity and pharmacological properties,for example,antitumor,antiviral activities and inhibition of the tuberculosis.The structure of the spirooxindole was easy for modification and could provide important molecular skeletons for drug development.This thesis aimed to develope new synthetic methods for the synthesis of new spirooxindole compounds.Starting from isatin,the nucleophilic addition to the C3 carbonyl of isatins provided 3-hydroxy-2-oxindoles,Oxidation with Jones reagent provided spirooxindoles.This thesis consists of three chapters.In Chapter 1,the biological activities of the 3-hydroxyoxindoles and oxygen heterocyclic oxindoles with similar structural framework were summarized.The synthesis of 3-hydroxy-oxindole as well as heterocyclic ring containing oxindole was also summarized.In Chapter 2,We have developed a new synthetic method for spiro oxindole compounds.After the nucleophilic addition of phenyl lithium to the C3 carbonyl of isatin,the 3-phenyl-3-hydroxyoxindoles were obtained.Deprotection and oxidation with Jones reagent provided spiro-oxindoles.Finally,the spiro oxindoles were transformed to aniline derivatives.In Chapter 3,Experiment procedure,physical and spectrum data for compounds described in Chapter 2 are recorded.