Solid-Phase Organic Synthesis of Heterocyclic Compounds Based on Polystyrene-Supported Sulfonyl Compounds
|School||Jiangxi Normal University|
|Keywords||Solid Phase Organic Synthesis Sodium polystyrene load Polystyrene load 3 - butene / alkynyl sulfone Vinyl- substituted isoxazole ( morpholino ) The sulfonyl methyl acetate polystyrene load Tri-substituted 1,2,4 - triazolo The sulfonyl Titanium polystyrene load Vinyl - 1 ,2,4 - oxazolyl|
In this paper explores the load several polystyrene sulfonate preparation and their participation in the solid-phase organic synthesis reactions of heterocyclic compounds . 1 Sodium load 1% divinyl benzene crosslinked polystyrene resin with methyl iodide Synthesis of polystyrene - supported methyl sulfone , followed by dimethylsulfoxide ions with allyl bromide or propargyl bromide , prepared polystyrene load 3 - butenyl sulphoxide or 3 - butyn- sulfone reagent , respectively , with a nitrile oxide , 1,3 - dipolar cycloaddition reaction to give 5 - (2 - benzenesulfonyl- ethyl)- isoxazol- ( morpholino ) resin , followed by reaction at room temperature , triethylamine eliminate , in good yield ( 74-84 %) and high purity ( 90-95% ) to obtain a vinyl - substituted isoxazoline or a vinyl - substituted isoxazole derivatives , this method has the advantages of simple operation, mild reaction conditions . (2) Synthesis of 1% crosslinked polystyrene load alkylene sulfonate resin and methyl bromoacetate reaction the sulfonyl methyl acetate reagent polystyrene load further hydrazine solution obtained with an acid chloride prepared by the reaction sulfonyl - containing bis - hydrazide reagent , and subsequently with aryl amine , aryl coupling of nitrogen and phosphorus in o-dichlorobenzene was heated under reflux reaction sulfonyl methyl 1,2,4 - triazol- resin cyclization , and then iodomethane alkylation reaction by eliminating or reducing reaction , a sulfonyl group from the resin dissociation down, to provide a solid-phase synthesis of tri-substituted -1, 2,4 - triazole derivative , and a yield of 72-75 % . the crude product was not purified before the purity of 90-94 % . 3 with 1% crosslinked polystyrene the Sodium resin load and bromoacetate Built the obtained polystyrene sulfonyl load Titanium reagents, then in the presence of dicyclohexyl carbodiimide (DCC) , the reagent with the amidoxime condensation to give the sulfonyl methyl- substituted 1,2,4 - oxadiazole compound resin , and then an alkylation reaction with iodomethane , and finally liberated with triethylamine , to give a vinyl substituted 1 , 2,4 - oxadiazole compounds. This method is simple , high yield ( 74-82 % ) , the purity of the crude product was purified before more than 90% .