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Electrochemically Generated Nitrogen-Centered Radicals Cascade Cyclization For The Synthesis Of Polysubstituted Benzoheterocycles And 7-membered Carbocycles

Posted on:2019-07-27Degree:MasterType:Thesis
Country:ChinaCandidate:H LongFull Text:PDF
GTID:2381330548950837Subject:Organic Chemistry
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N-heterocycles are ubiquitous motifs that play a critical role in both medicinal chemistry and biology.Therefore,the development of simple,efficient methods for their synthesis is an important research focus for organic chemists.Nitrogen-centered radicals are versatile intermediates for the construction of nitrogen-containing compounds.We report herein the electrooxidative method to produce amidyl radicals from N-arylamides.Based on this radical-generating method,the constructing of N-heterocycles,including benzimidazolones,benzoxazolones and 7-membered carbocycles through cascade radical cyclization has been developed.This dissertation is divided into the following sections mainly:Herein,we report an electrooxidative approach to access amidinyl radical intermediate that subsequently participates in a 6-endo-dig cyclization to give the vinyl radical,which then undergoes a second cyclization with the alkene to afford the N-heterocycles.Valuably,the method we developed could achieve de novo synthesis of polysubstituted benzimidazolones and benzoxazolones efficiently.(?)Radical cyclization reactions have become an indispensable tool for the synthesis of cyclic structures.Among these reactions,those that form 7-membered carbocycles remain rare probably because of the 7-endo radical-cyclization processes are disfavored than 6-exo processes.Herein we disclose an electrochemical method for the synthesis of 7-membered carbocycles via 5-exo-trig/7-endo-trig cascade radical cyclization.(?)...
Keywords/Search Tags:electrochemistry, nitrogen radical, aromatizatian, 7-membered carbocycles
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