Construction Of [2,3-b]indole Fused Cycles By Reaction Of Bisdiazoisatin

[2,3-b] indole fused rings are a crucial kind of alkaloids with potential biological activity that exist in a number of natural products and drug molecules,and they also have wide application in light-emitting functional materials due to their conjugated structure.Therefore,it is of great significance to develop a new synthetic route to construct them.Diazo compounds are an important class of synthons in the construction of cyclic skeleton structures.They are often used as carbene precursors.By taking advantage of their diverse reactivities,chemists could design various reactions to synthesize a series of novel compounds.In this paper,bisdiazoisatin is used as an efficient synthon to synthesize indolo[2,3-b]indole fused ring compounds.As potential organic light-emitting functional materials,4H-indo[2,3-b]indole skeleton compounds have very important research value,but there are only few reports on their synthesis.In the second chapter of this thesis,a tandem reaction of bisdiazoisatin and cyclic enamine ketone involving carbene insertion/[3+2] cycloaddition intermolecular cyclization/ring-opening occurred in the presence of rhodium acetate,thus delivering a series of 4H-indolo[2,3-b]indoles in up to 55% yield.This methodology has provided an efficient and reliable approach to 4H-indolo[2,3-b]indoles via new C-C and C-N bonds forming processes.The third chapter of this thesis deals with the carbene insertion/nucleophilic addition/proton migration/intramolecular cyclization/isomerization sequence of bisdiazoisatin and tryptophol under the catalysis of [RhCH₃?CH₂?₆CO₂]₂.These transformations not only have achieved the bifunctionalization of tryptophols at both the C2-and C3-positions,but also made an exquisite intergaration of biologically interesting 4H-furo[2,3-b]indole and 2H-oxazolo [3,2-a] indole into one molecule.