The Solid Phase Synthesis Of Isoxazoles And The Friedel-Crafts Alkylation Of Hydrazine With Olefins Are Supported By Polystyrene-loaded Selenium Reagents

Polystyene-supported organic selenium reagent was prepared,then the solid-phase synthesis of dihydronaphthalenyl methyl isoxazole by 1,3-dipolar cycloaddition reaction and the solid-phase synthesis of phenylvinyl indole by Friedel-Crafts alkylation reaction of indole with olefins were studied.Firstly,isoxazole compounds are used not only in organic synthesis as an important organic intermediate,but also in the preparation of some important bioactive compouds such as herbicides,insecticides,fungicides,pesticides,etc.It's important to improve the structure of isoxazole molecule to optimize its bioactivities.Many dihydronaphthalene derivatives have a variety of pharmacological activities such as anti-inflammatory,analgesic and antipyretic,etc.By the 1,3-dipolar cycloaddition of alkenyl dihydronaphthalene with 1,3-dipoles,isoxazole ring was brought into the structure of dihydronaphthalene molecule to obtain more species of bioactive compounds.The formation of intramolecular carbon-carbon bonds of the 1-phenyl-4-cyano-4(3,4-dimethoxy)phenyl-1-butylene was induced by N-polystyrene-supported seleno-succinimide in the presence of a catalytic amount of trimethylsilyl trifluoro-methanesulfonate to obtain intermediate resin,3-(polystyrene-supported selanyl)-1,2,3,4-tetrahydronaphthalene-1-carbonitrile.After the treatment of the intermediate resin with allyl bromide and sodium ethoxide,and then with substituted benzo-hydroximoyl chloride and triethylamine,4,5-dihydroisoxazol-5-yl)methyl-3-(polystyrene-supported selany])-1,2,3,4-tetrahydronaphthalene-1-carbonitrile was obtained.The product,4,5-dihydroisoxazol-5-yl-methyl-1,2-dihydronaphthalene-1-carbonitrile,was synthysized by subsequent elimination reaction of selenoxide.Secondly,in the presence of p-toluenesulfonic acid,vinyl indole was synthesized by N-polystyrene-supported selenosuccinimide-induced Friedel-Crafts alkylation reaction of indole and olefin at room temperature and subsequent elimination reaction of selenoxide.New carbon-selenium bond and carbon-carbon bond formed in the Friedel-Crafts alkylation reaction with high regioselectivity.