Study Of Domino Reactions For The High Efficient Construction Of Indole Derivatives Based On Ylide

Indoles and Oxoindole derivatives have broad biological activity and potential medicinal value.Therefore,it is very important to develop new and efficient synthetic methods for indole compounds.In this paper,indole derivatives were used as substrate substituted indole derivatives were synthesized by combining with the active ylides with multiple reaction sites.Four new Domino reactions were completed,involving phosphorus ylide,sulfur ylides,azomethine ylides,For the synthesis of some heterocyclic compounds to provide new ideas and methods.1)First,a catalyst-free domino reaction was developed for the synthesis of 3-?cyclopentenone?oxindoles.This method is the first example of a phosphine-ylide-initiated Wittig/Michael addition/Wittig domino sequence.The mild reaction conditions and broad functional groups tolerance make it highly valuable for synthesizing 3-?cyclopentenone?oxindoles2)Second,A Cs₂CO₃-promoted Michael addition-[2,3]-sigmatropic rearrangement domino reaction between arenesulfonylindole and sulfur ylide has been developed.This reaction affords a facile method for the synthesis of 3-substituted indoles with a homoallyl sulfide moiety.In this domino sequence,two C-C bonds and one C-C bond cleavage were formed.3)Farther,A protocol for the direct functionalization of N-H /?,?,?,?-C?sp³?-H of piperidine without any metal or external oxidants is reported.This reaction is promoted by 4-?trifluoromethyl?benzoic acid via an azomethine ylide intermediate.This is a simple method for the synthesis of spirooxindoles bearing 3-substituted oxindole moieties.4)Final,On the basis of the above work,the ?-C-H functionalization of the acid-promoted azepane was continued to afford a spirocycloanoindole derivative containing a sevenmembered ring structure,This reaction is promoted by 4-fluorobenzoic acid via an azomethine ylide intermediate.which is a highly efficient synthesis of spirocyclic oxidized indole derivatives containing azepane moieties.