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Application Of TEMPO In The Carbon-Carbon Single Bond Construction Of Indole Derivatives

Posted on:2014-02-14Degree:MasterType:Thesis
Country:ChinaCandidate:W B QinFull Text:PDF
GTID:2251330392463041Subject:Organic Chemistry
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indole skeleton alkaloids are widespread in nature and exhibit significant biological activity,In particular,2-substituted and3-substituted oxindoles are prevalent in a wide array ofbiologically relevant natural products, therefore, the research on indoles is still an active area. Thispaper is mainly engaged in the methodology synthesis of2-substituted and3-substituted oxindolederivatives, and aimed at achieve high regioselectivity.In the first chapter, The progress of C2,C3Activation of indole and oligomeric indolesynthesis research were Introducted and followed with a brief summary.In the second chapter, By way of exploration and optimitization of reaction condition basedon the catalyst of TEMPO. A scope of the reaction was studied and a variety of trimer indolederivatives were generated. this synthesis method has the advantage of operationally simple,metal-free, environmentally benign and high regioselectivity.In the third chapter, shows a detail Sn(IV)-Catalyzed Cleavage of C-C Bond of indoletrimers to obtain unsaturated dimeric indoles, Cross coupling indole trimers was obtained afteraddition of substituted indoles to unsaturated dimeric indole. And the whole steps processed to a“one pot” reaction.In the fourth chapter, controlled regioselectivity by way of change reaction conditions for thegeneration of all-carbon quaternary centers at the C3position of indoles in moderate to excellentyields of3,3-disubstituted indole trimers by using TEMPO in Air. a possible mechanism wasproposed on the basis of preliminary discussion.In the fifth chapter, provides an alternative approach for the direct generation of tertiarycarbon centers at the C3position of indoles by using TEMPO/AgNO3in Air. We also describedthe modifications of the typical reaction conditions, substrate studies.In the final chapter, we described a cross-coupling reaction of indoles with pyridines inaddition of (Boc)2O by using TEMPO in Air. The modifications of typical reaction conditions,substrate studies.
Keywords/Search Tags:TEMPO, quaternary centers, indoles, Trimerization, Cross-coupling
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