Study On Selectivity Of Addition Reaction Of Oxindole With Dienone Compounds

2-oxindole is a core backbone of a series of biologically active natural products and drug molecule,the unique chemical and biological activities of 2-oxindole has thus attracted the attention of organic chemists,medical scientist and biologist.Michael addition reaction is a very important organic reaction which the carbon anion connected with ?,?-unsaturated aldehyde,ketone,carboxylic acids,esters,nitriles,nitro compounds,etc.It is used to been grow carbon chains and Synthesis the various functional groups compounds,a commonly way of building carbon-carbon bonds.In recent decades,many 2-oxindole derivatives have been synthesized by modification of the 3 position of 2-oxindole.For one things,Many pharmaceutically active structures were found;for the other thing,it could been useful to solve the structure-activity relationship.The new 2-oxindole derivatives was synthesized by Michael addition reaction of 2-oxindole with 1,4-dien-3-one in this paper.The spirocyclic oxindoles were synthesized by Michael addition reaction of 2-oxindole with(1E,4E)-1,5-diarylpenta-1,4-dien-3-one,spirocyclic oxindoles were obtained in good yield(up to 99%)and excellent diastereoselectivity(up to 90:8:2)by using potassium acetate and tetrabutylammonium bromide.Trimethylsilane is an active group that can be used to modify compounds,the power supply and steric hindrance of the trimethylsilyl also inhibited the Michael addition reaction.3-Dialkylated 2-oxindole derivatives were synthesized by Michael-Michael addition of2-oxindole with(E)-1-(trimethylsilyl)penta-1,4-dien-3-one by using the potassium acetate and tetrabutylammonium bromide(up to 99%);and the spirocyclic oxindoles were synthesized by Michael-Michael-Alodol addition by using the Potassium hydroxide and Tetrabutylammonium bromide(up to 83%).