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Studies On The Green Synthesis Of Alcohols And The Construction Of Some Active Heterocyclic Structures

Posted on:2020-06-01Degree:MasterType:Thesis
Country:ChinaCandidate:H C LiuFull Text:PDF
GTID:2381330578459045Subject:Chemistry
Abstract/Summary:PDF Full Text Request
Azacyclic organic compounds are widely found in physiologically active drugs and natural products,It is also an important intermediate in organic synthesis.In the reported literatures,the C-N bond construction method has drawbacks such as noble metal catalysis,high toxicity of raw materials and harsh reaction conditions.The development of green catalytic synthesis method is more consistent with the concept of sustainable development of modern organic synthesis.Therefore,it is very important to synthesize heterocyclic compounds by efficient,green and simple methods.The green synthesis of alcohols and the synthesis of nitroheterocyclic compounds such as carboline derivatives and benzimidazole derivatives will be studied in this paper.It is mainly composed of three parts: ?.Study of halogenated alkanes hydrolysis to alcohol accelerated by complete oxygen transfer promoted by DMSO;?.Study on Construction of heterocyclic ring structures of tetrahydrogen-?-carboline and ?-carboline;?.Green synthesis of benzimidazoles catalyzed by impurities.Part ?: On the basis of a large number of literature studies,we developed a green synthesis method of organic halide hydrolysis to alcohol promoted by DMSO under neutral conditions.The reaction proposed that DMSO promoted complete oxygen transfer to enhance the nucleophilic of water,and DMSO participated in the conversion cycle and could be recovered and reused during the reaction process,which has potential application value in practical industry.Part ?: The recent progress in the synthesis of tetrahydrogen-?-carboline and ?-carboline is reviewed.These methods include the traditional condensation of aldehydes and ketones with amines,the aromatization of aniline halides,and the [4+2] cycloaddition of imide compounds with acetylene.The oxidative condensation reaction of alcohol and tryptamine catalyzed by TEMPO/TBN was developed to selectively obtain tetrahydro-?-carboline and ?-carboline heterocyclic ring structures without metal participation.Part ?: This paper reviews the progress in the literature on the synthesis methods of benzimidazoles,including the reactions of o-phenylenediamine with aldehyde substrates,o-phenylenediamine with carboxylic acid and its derivatives as substrates,and the reactions of o-phenylenediamine with alcohol substrates.The new concept of impurity catalysis is proposed,which is suitable for green and sustainable development.
Keywords/Search Tags:alcohol, halogenated hydrocarbon, DMSO, TEMPO/TBN, tryptamine, tryptophan, ?-carboline, benzimidazole
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