New Syntheses Of Bis(indole) Methane Sulfide Derivatives

Indole and its derivatives are a kind of important organic small molecules,the key structural units frequently were found in bioactive molecules.Among them,the bis(indole)methane derivatives have the functions of anti-bacteria,anti-fungi and the toxic effects of anti-leukemia cells.At present,there are several kinds of synthetic methods of bis(indole)methane derivatives.Most of the ways were reported are condensation reaction of indole and its derivatives with carbonyl compounds under the catalyst of acids,the varieties of corresponding bis(indole)methane derivatives are rich,but the synthetic methods of bis(indole)methane sulfide derivatives are very limited.The research work of this thesis is:five new bis(indole)methane sulfide derivatives and two mixture of bis(indole)methane sulfide derivatives were synthesized by reacting vinyl sulfoxide activated by trifluoroacetic anhydride with indole and its derivatives,under nitrogen atmosphere.Under the optimized synthetic conditions:n(vinyl sulfoxide):n(2-chloropyridine):n(indole)= 1:2:3,at-78 ? to room temperature for 50 h,the yield of bis(indole)methane sulfide derivative is up to 41%.The synthetic method is a novel,simple one.3-substituted indole derivatives can be synthesized by the Michael addition reaction of indole and its derivatives with a,(3 unsaturated carbonyl compounds or nitroolefins as Michael acceptors in the presence of catalysts.However,the reaction of using vinyl sulfoxide as Michael receptors has not been reported.In this paper,under the catalysts of protonic acids and Lewis acids,we try to obtain 3-substituted indole sulfoxide derivatives by using conjugate addition reaction:vinyl sulfoxide as Michael receptors,indole as nucleophilic reagent,which work has not been successful yet.