Oxidative Cyclization Of Ortho Acyl The Iodosodiacetate Triggered With Tetrabutylammonium Iodide Compounds Of The Substituted Phenols And Anilines

This thesis focused on the tandem acetoxylation-cyclization reaction of o-acyl phenols and anilines. It has reported the synthesis of benzofuranones and 3-oxyindoles under the condition of PhI(OAc)2/TBAI. Also, it has introduced a new method for the construction of oxa-aza spirobicycles.In the first part, under the condition of PhI(OAc)2/TBAI, we investigate the tandem cyclization reaction with the substrate of o-acyl phenols and synthesize the benzofuranones which are the important structural components of many medicinally and biologically active natural and unnatural substances. We also supposed the mechanism of the reaction is to yield theα-acetoxylation intermediate first, and then the intermediate will be cyclized and gained the desire products.Next, under the same condition, we use the 4-methyl-N-(2-propionylphenyl)-benzene sulfonamide as the reaction substrate and successfully synthesize the 3-oxyindoles. The reaction mechanism is the cyclization of the substrate first and then the acetoxylation, which is different from the phenols. Also, we test the Friedel-Crafts reaction of a-Acetoxy Indolin-3-one and the results turn to be gratifying.Finally, under the condition of PhI(OAc)2/TBAI, we successfully construct the oxa-aza spirobicycles via a tandem carbon-hydrogen bond oxidation. We have already confirmed its structure with the X-ray Diffraction. The scope of the substrate is continued to be tested.