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The Studies On The Synthesis Of Benzimidazole Compounds And 1,2,4-triazole Compounds

Posted on:2018-01-02Degree:MasterType:Thesis
Country:ChinaCandidate:H L LiFull Text:PDF
GTID:2321330512491725Subject:Chemistry
Abstract/Summary:PDF Full Text Request
Benzimidazole derivatives are one of the most important classes of nitrogen-containing heterocyclic compounds ubiquitously existed in a myriad of natural products and synthetic products,as the core structural units of a variety of drugs and significant biological activity.Considering the unique property,reactivity,physiological activity and great utility value of benzimidazole core,the development of facile and straightforward strategies for their synthesis is of great significance.In this paper,we have disclosed an approach for the rapid assembly of benzimidazole derivatives from readily accessible N-alkyl-2-iodoaniline and sodium azide in the presence of copper catalysts.The methodology features has a broad substrate scope,mild reaction conditions,accessible and cheap catalyst.Cu I was regarded as a versatile catalyst to trigger the SNAr reaction and to assist single-electron-transfer oxidation process,as well as promote the subsequent denitrogenation/cyclization sequences.1,2,4-Triazoles,as highly privileged heterocyclic scaffolds,have been found extensive applications in biological and pharmaceutical fields as well as materials science.The compounds with 1,2,4-triazoles as the core framework have been widely used in the field of biology,medicine and materials science.1,3,5-triaryl substituted 1H-1,2,4-triazoles has also attracted much interest in material science including application in the fields of solar cells,image sensors,dye lasers,and electroluminescent devices.Therefore,general and straightforward methods to their synthesis are highly desirable,and a series of synthetic strategies of 1,2,4-triazoles have been developed.In this paper,we have developed a highly attractive strategy for rapid and efficient construction,in a metal-free mediated intermolecular fashion,of molecules containing 1,2,4-triazole moieties from hydrazones and amines.The methodology features readily accessible starting reagents,general and convenient operating conditions,a broad substrate scope,and high efficiency.The reaction can be easily scaled up to gram scale,thereby providing the possibility for the scaled production of structurally diverse 1,2,4-triazoles.The synthetic utilization of our methodology is illustrated by the expedient synthesis of fluorene-triazole compound and the photophysical property of compound was tested by fluorescence measurements.This result implied that the fluorene-triazole compound had a potential application in the field of fluorescent material.
Keywords/Search Tags:Copper catalyst, Benzimidazoles, Iodine, 1,2,4-Triazoles, Hydrazones
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