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Study On The Synthesis,Reacting System Of Novel Derivatives Of Di-N-oxoquinoxaline Formaldehyde And Their Biological Activity

Posted on:2005-11-08Degree:DoctorType:Dissertation
Country:ChinaCandidate:J Z MaFull Text:PDF
GTID:1101360125969116Subject:Agricultural Products Processing and Storage
Abstract/Summary:PDF Full Text Request
It is one of the indispensable factors to produce green food that the no poisonous no remaining safe herbicide bacteria inhibitors and feed addictives are used. This is very important also for storage and process of agricultural products maintaining the quality of food and development of aquaculture.Compounds of quinoxaline di-N-oxides, which were the pre ones having anti-bacteria anti-cancer activity, was found in the 50s last century. Scientists have been researching for their organic activity as the animal growth promoting agents from the 70's and the medicines from the 90's. Many of documents show that those compounds are low remaining safe to human being and animal.So far, the study on this compounds has been focused on those derivatives of quinoxaline di-N-oxides, such as hydrocarbon radical derivatives formic ether and formic amide. Study on organic activity is only in the fields of inhibiting bacteria feed addictive and medicine. The documents indexed by information indexing center of Agricultural Science Institute Hubei Province showed that the paper has not been found to use those compounds as farm chemicals, for example the herbicide.This paper probed a kind of novel derivatives of di-N-oxoquinoxaline formaldehyde, such as schiff base hydrazone etc for their synthesis herbicidal activity inhibiting bacteria activity and promoting animal growth activity. It is the first time to study and report the best synthesis route factors of affecting the reaction systems structure characterizing and synthesis mechanism of the novel active compounds. The experiments in the herbicidal activity inhibiting bacteria activity and promoting animal growth activity of these novel compounds are also first studied. It lays a solid base on theory for applying the compounds.This paper has done work as follow: 1. Choice of the methods for Synthesis of New CompoundsThis paper designed 7methods for synthesizing new compounds and tested them one by one. It gained the best one with moderate reacting conditions and higher yield. It is that the ortho-nitroaniline is oxidized by NaCIO and changes into benzofurazan-N-oxide (BFO); then BFO reacts with acetone and changes into 2-methyl quinoxaline di-N-oxide; 2-methyl quinoxaline di-N-oxide is oxidized by selenium dioxide again and changes into 2-methyl quinoxaline formaldehyde di-N-oxide; 2-methyl quinoxaline formaldehyde di-N-oxide reacts with RNH2 and R- NHNH into the compounds, as formula 1 and formula 2 show.2. Study on two reacting systemsThe key reactions are ( 2) and (3 ) among those ones elected. Components in the two reacting systems were analyzed with Chromatography-Mass Spectrograph to distinguish the main factors of effecting the yield probe the second reaction mechanisnu improve reacting conditions and promote the yield, inspect the poison of the side-product (the side-product maybe into product in the third reaction especially) for development in future also . There are 16 and 17 components in the two systems respectively. Those components have been recognized according to the theory about organic reaction and the spectrograms. The mechanism of synthesizing methyl quinoxaline di-N-oxide has been put forward and the side reaction causes suggested.The mechanism is as follows: the catalyst amine reacts with acetone and changes into amine-acetone complex, which attacks the BFO nucleophilically and linking acetone & BFO, then the intra-molecular rearrangement and nucleophilic substitution occurs in succession; finally, after deammoniation and elimination takes place, the product forms.It makes the side-products come into being that there are nucleophilic reagent oxidizer and water in the system, in addition, the influence of the light the heat and the vinylogy, the nucleophilic choice not very distinctively in the system.There are oxidizer water acids reducer coming from reaction, the influence of the light the heat also in the system of synthesizing methyl quinoxaline formaldehyde di-N-oxide. It makes the side reaction of hydrolysis rearrangement mi...
Keywords/Search Tags:Derivatives of quinoxaline di-N-oxides formaldehyde, Synthesis, Structure characterized, Reaction mechanism, Reaction condition improving, organic activity, Quantitative analysis of derivatives
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