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Study On Highly Stereoselective Synthesis Of 3-methoxyisoindoles And Their Derivatives Via DMAP Catalyzed Cyclization Of Methyl 2-alkynylbenzimidates

Posted on:2020-05-06Degree:MasterType:Thesis
Country:ChinaCandidate:X J LiangFull Text:PDF
GTID:2381330602460142Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
3-Methoxyisoindoles and their derivatives are very important fived-membered heterocyclic compounds.They are not only the core structural unit of many natural products and drug molecules,but also important intermediates in organic synthesis.In this paper,isoindoles derivatives were synthesized by N,N-dimethylpyridin-4-amine(DMAP)catalysis with high stereoselectivity based on the electrophilic cyclization reaction.The first chapter focuses on the following two aspects:(1)the application of isoindoles and its derivatives in antiviral,anti-inflammatory,antibacterial,anti-cardiovascular disease,anti-tumor and other aspects;(2)the many synthetic methods of isoindoles and isoindolinones compounds.The second chapter is about the motivation of this project.In the third chapter,methyl 2-alkynylbenzimidates were used as model to optimize the reaction conditions(catalyst,temperature and solvent).Then under the optimal reaction conditions,various substituted 3-methoxyisoindoles have been synthesized.In addition,the proposed mechanism for the DMAP catalyzed cyclization of methyl 2-alkynylbenzimidates was shown.Finally,the 3-methoxyisoindoles products can be efficiently converted to corresponding 3-methyleneisoindolin-1-ones,3-benzylisoindolin-1-ones,1-benzyl-3-methoxy isoindoles and 3-amino-1-methyleneisoindoles.
Keywords/Search Tags:cyclization, imidate, 3-methoxyisoindole, stereoselective, N,N-dimethylformamide
PDF Full Text Request
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