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Study On Aldimine Oxidative For Synthesis Of Amides And P?NMe2?3-Mediated [2+1] Annulation Reaction

Posted on:2018-02-09Degree:MasterType:Thesis
Country:ChinaCandidate:Q P LiuFull Text:PDF
GTID:2321330533970231Subject:Organic Chemistry
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In the first part of this dissertation,the Kukhtin-Ramirez adducts as 1,1-dipoles in organic reactions was reviewed.Isatins and ?-Ketoesters were used as substrates to generate Kukhtin-Ramirez adducts in situ by P?NMe2?3.In the second part,we have also developed a P?NMe2?3-mediated reductive [1 + 2]-cycloaddition reaction of isatins with ?,?-unsaturated amides,which p rovides a facile and efficient synthetic method for spirocyclopropyl oxindoles in up to 99% yield with 16:1 dr.This reaction promotes from the reactivity of Kukhtin-Ramirez adducts serving as 1,1-dipoles.In the third part,we have described a new protocol for aziridination of cyclic Nsulfonyl imines with isatins.This P?NMe2?3-mediated coupling reaction of Kukhtine-Ramirez adducts captured by cyclic N-sulfonyl imines is first reported,and it may serve as a useful complement metods for synthesis of complex aziridination derivatives.In the fourth part,a new synthetic approach toward amides from aldimines in the presence of Oxone as oxidant has been developed under transition-metal-free conditions.These oxdative reactions proceed with outstanding yields under simple conditions and minimum experimental manipulation.The method has been applied to the synthesis of cyclic and acyclic N-sulfonyl imines as well as N-alkyl,and N-aryl imines.This reaction may be an alternative to the classical methods for preparing amides.In the last part,the summary is presented in this dissertation.
Keywords/Search Tags:1,2-dicarbonyl compounds, amides, Baeyer-Villiger, Aziridination, [2+1] annulation
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