Biomimetic Synthesis Of Mannich Base And Aldehyde New Method

Nowadays, the biological functions of tetrahydrofolate coenzymes have increasingly caught scientists'attentions, whose use in biomimetic synthesis has especially become an important subject of biochemistry. With an active part similar to 1,2-diaminc in structure, the tetrahydrofolate coenzymes, which are the carbon source of the methylation for many materials in the living body, carry on the function of transferring one-carbon unit for the biosynthesis and metabolism. The biomimetic organic synthesis of tetrahydrofolate coenzyme is to select the appropriate compounds, based on the active part that plays a significant role in the coenzymes, as the tetrahydrofolate coenzyme models, and to imitate the one-carbon unit in tetrahydrofolate coenzymes. The model compounds can transfer one-carbon fragment to some reaction systems at different oxidation states, which will provide a new way to synthesize various organic compounds and some bioactive substances.Mannich bases and its derivatives, which are useful in various fields of human life-material production, have extensive biological activity. Many Mannich base derivatives possess such biological functions as anticancer, anti-inflammatory, antimicrobial, anticonvulsant or antiemetic activity, thus they are widely used in pharmaceutical industry. As a result, the synthesis of Mannich base derivatives has always been hotspot issues at home and abroad. In this paper, on the basis of the existing research work and the latest research progress at home and abroad,1,3-dimethylimidazolidine was persented as a new tetrahydrofolate coenzyme model at formaldehyde oxidation state. Meanwhile,1, 3-dimethylimidazolidine in Mannich reactions was studied, the process of one-carbon unit transfer through the model was researched, a novel biomimetic synthetic method preparing Mannich bases was realized, and the mechanism was discussed.Aldehyde is a kind of versatile compounds in organic synthesis. They are occupying an important position not only in the basic research of organic chemistry, but also in practical applications. In this paper, according to the tetrahydrofolate coenzyme model that was once put forward by our research team, the transformation of the coenzyme model from 1, 3-dimethylbenzimidazolium as the formic oxidation state to 1,3-dimethylbenzimidazolidine as the formaldehyde oxidation state was firstly realized with sodium/ethanol reduction system, then acidic hydrolysis was used to obtain aldehydes, thus a novel biomimetic synthetic method of aldehydes was provided. The mechanism on the reduction of benzimidazolium salts with sodium/ethanol system was also discussed.