Preparation Of Polystyrene-supported2-sulfonylethanol And Its Application In Solid-phase Organic Synthesis

In this dissertation, preparation of several novel polystyrene-supported2-sulfonylethanol and vinyl sulfone reagents and their applications in solid-phaseorganic synthesis of compounds were investigated.Firstly, reaction of1%divinylbenzene-styrene copolymer supported sodiumphenylsulfinate with2-chlorethyl alcohol afforded polystyrene-supported2-sulfonylethanol reagent, which was further treated with phonols promoted byDIPDA/PPh3/NMM and subsequent elimination with DBU to provide a novel,convenient, wild solid-phase organic synthetic method for aryl vinyl ethers in goodyields (88-95%).Secondly, treatment of the polystyrene-supported2-sulfonylethanol reagent withmethanesulfonyl chloride in the presence of triethylamine yielded the correspondingpolystyrene-supported vinyl sulfone. Then reaction of vinyl sulfone resin with sodiumazide and aryl halide promoted by copper(I) iodide formed the polymeric1-substituted-4-phenylsulfonyl-4,5–dihydro-1H-1,2,3-triazole intermediates,which was further treated with an excess of potassium tert-buoxide at ice-bath tofurnish1-substituted-1,2,3-triazole. The advantages of this method are mild reactionconditions, easy operation, good yields (54-97%) of products.Finally, treatment of the polystyrene-supported vinyl sulfone reagent with nitrileoxides generated in situ from oximes and N-chlorosuccinimide (NCS) afforded thepolymeric3-substituted-5-phenylsulfonyl-isoxazoline, which was further cleavedusing conditions as above to generate3-substituted-isoxazole in good yields (73-94%)with simple operation and isolation.