The 2-aminoindanone And Indoline Spiro Compounds Were Constructed By The Tandem Cyclization Of Aziridine

2-aminoindanones and spiroindoline scaffolds represent privileged structures encountered in a lot of natural products,as well as synthetic compounds with interesting biological properties.The development of synthetic methodologies toward these highly useful heterocyclic compounds has drawn much attention from synthetic organic chemists.Therefore,the development of novel and simple synthesis of these two kinds of compounds has also attracted widespread attention from chemists.In this thesis,we mainly introduce the efficient construction of 2-aminoindanones and spiroindoline compounds by using the domino reaction of different aziridines.In the first work,we designed and synthesized a kind of substrates containing both N-sulfonyl aziridines and electron-deficient alkenes,and developed a In(OTf)₃-catalyzed the domino reaction involving sequential oxidative ring opening of aziridines by using the solvent dimethyl sulfoxide and intramolecular Michael addition to synthesize a series of 2-aminoindanones by the formation of one new C=O bond and one new C-C bond.The significant advantages of this strategy included the highly functionalized products,excellent diastereoselectivities,mild conditions and broad substrate scopes.The catalyst In(OTf)₃ plays an important role in the formation of the indanone ring.In the second work,we designed a new strategy for the synthesis of spirocyclic compounds.we designed and synthesized a new type of 2,2-disubstituted N-sulfonyl aziridine compounds.Alcohols and arenes are simultaneously introduced to the two different substitutions of the aziridine ring.This domino reaction involves ring opening of aziridine and C-H activation/cyclization to synthesize spiroindoline compounds.The advantages of this strategy included good atom economy,high bonding efficiency and cyclization efficiency,broad scope of substrates and good generality of the ring size in products.The two domino reactions have the advantages of high atomic utilization,simple operation,wide substrate range,and environmental friendliness.They provided a good choice for the general and efficient construction of 2-aminoindanones and spiroindoline skeletons,which was particularly well suited for the preparation of2-aminoindanone and spiroindoline compound libraries.