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Study On Synthesis Of Five/Six-membered Nitrogen Heterocyclic Compounds With Ortho-acylarylisocyanides

Posted on:2019-07-21Degree:MasterType:Thesis
Country:ChinaCandidate:J J LiFull Text:PDF
GTID:2371330572460788Subject:Chemistry
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Isocyanides are a class of organic compounds containing divalent carbon atoms.The unique features of isocyanides whose electrophilic and nucleophilc centers are the same have turned them into potent building blocks for various synthetic reaction,such as multicomponent reactions,,?-addition.,insertions reactions.In recent years,the use of isonitrile to build nitrogen-containing heterocyclic compounds has developed rapidly and great achievements have been made.In this paper,we designed two kinds of isocyanides-based ?-addition and insertion reaction to produce N-heterocyclic compounds with high efficiency.Based on the developde two kinds of reactions,we have achieved that cycanative indoles and quinazolines.In chapter one,the reactions involved in isonitrile and isonitrile were briefly described,and the method of building nitrogen-containing heterocyclic compounds based on isonitrile was introduced.The chapter two,we described the application and synthesis progress of indolin-3-ol derivatives in recent years and introduced silver-catalyzed ?-addition of ortho-acylarylisocyanides with ?-dicarbonyls: A facile method to 2-methyleneindolin-3-ols.A series of 2,3-substituted indolin-3-ols derivatives were synthesized efficiently by silver-catalyzed by tandem intermolecular ?-electrophilic addition/intramolecular?-nucleophilic addition of 2-isocyanophenyl ketone and various 1,3-dicarbonyl compounds.The chapter three,we described the application and synthesis of quinazoline derivatives in recent years and introduced silver-catalyzed [5 + 1] annulation of o-acylaryl isocyanides with ammonium acetate and hydroxlamine was developed for the efficient and practical synthesis of quinazolines and quinazoline 3-oxides in good to excellent yields,respectively.The domino process involved an unprecedented isocyanide insertion into the N-H bond of ammonia or hydroxylamine and followed by condensation reaction at ambient conditions.The chapter four,summarizes the main work of this paper and prospects the research prospects of this subject.
Keywords/Search Tags:isocyanides, nitrogen heterocycles, indoles derivatives, quinazoline derivatives, insertion into the N-H bond
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