Study On Isocyanide And Gem-diactivated Olefine Based Domino Reactions

Isocyanide-based domino reactions have been highlighted as one of researchfrontier, widely used for the construction of heterocycles, total synthesis of naturalproducts, drug discovery and materials science. In this paper, novel domino reactionswere developed for the synthesis of structurally diverse pyrrole, indole and chromenederivatives in good to excellent yields under mild conditions.Polysubstituted pyrroles have a broad spectrum of biological activities, some ofthem are important intermediates in organic synthesis. Domino reactions fromisocyanides, gem-diactivated olefins with nucleophiles are efficient strategies for thesynthesis of polysubstituted pyrroles. In this paper, a multicomponent domino reactionfor the highly efficient chemoselective synthesis of polysubstituted pyrroles fromreadily available isocyanides, primary or secondary amines, and gem-diactivated olefinshas been developed.Polycyclic spiroindoline is the core skeleton of many natural products, which oftenexists in both alkaloids and pharmaceutical molecules. It is a great challenge to developsimple and efficient approaches to these kinds of complex molecules. In this paper, acatalyst-free one-pot domino reaction between2-isocyanoethylindole and gem-diactivated olefins for the construction of polycyclic spiroindolines was developed. Thismethod offers a straightforward access to polycyclic spiroindoline derivatives in highyields with excellent levels of diastereoselectivity.Diversity-oriented synthesis (DOS) allow for the rapid generation of libraries oforganic molecules. Isocyanide-based domino reactions are efficient synthetic strategiesfor the construction of heterocycle skeletons. In this paper, we developed a novel one-pot tandem reaction for the highly efficient synthesis of polysubstituted4H-chromenederivatives. In order to avoid the formation of by-products,4-(2,2-dicyanovinyl)benzoic acid was condensed with1,3-dicarbonyl compounds. Without isolation, equal amount of aldehydes and isocyanides were added into the mixture, providingpolysubstituted4H-chromene derivatives.