A kind of method that adopts aldoxime to ring-forming aziridine compound

Abstract

The invention discloses an aziridine compound cyclizing method adopting an aldoxime and belongs to the technical field of organic synthesis. According to the method, an aziridine compound activated with tosyl is adopted as an initial raw material, the aldoxime is adopted as a nucleophilic reagent, and the aziridine compound is subjected to cycloaddition in acetonitrile or chloroform under the catalytic functions of potassium hydroxide, potassium carbonate, potassium tert-butoxide or triethylamine. Reaction processes of the method are simple. The method adopts the potassium hydroxide, the potassium carbonate, the potassium tert-butoxide or the triethylamine as a catalyst, and adopts the acetonitrile or the chloroform as a solvent. The method is high in environment protection performance, mild in conditions and wide in universality. High yields and good regioselectivity can be achieved for aziridine compounds with different structures and aldoximes with different structures.

Description

technical field [0001] The invention relates to a method for forming rings of aziridine compounds by using aldoxime, and belongs to the technical field of organic synthesis. Background technique [0002] Aziridine compounds are important building blocks and intermediates in organic synthesis. They exist in many natural products and have good antiviral, antitumor and other biological activities. Aziridine can undergo a series of important reactions, such as ring-opening reaction, cycloaddition reaction, reduction and elimination reaction, etc. Its cycloaddition reaction can be used to synthesize five-membered or six-membered ring compounds, and then synthesize many compounds with biological activity and application prospects in the pharmaceutical and chemical industry. [0003] Reports on the ring-opening reactions of nucleophiles and aziridines have been common, but people’s enthusiasm for research on aziridine-related reactions remains undiminished. Among these numerous re...

AI Technical Summary

Problems solved by technology

This method first utilizes N-hydroxyl imine benzyl chloride to react with aziridine to generate azacyclo-1-yl phenyl ketone oxime, which is then reacted with trimethylchlorosilane under the catalysis of scandium trifluoromethanesulfonate. The oxadiazine derivatives were obtained under the following conditions; then the author expanded the various substrates under the optimal reaction conditions obtained by the optimization screening, and the result was that all the substrates could be converted into the desired The oxadiazine compound, finally the author directly reacts N-benzyl-2-methylaziridine with oxime in dichloromethane to generate the desired product (45%), because the yield is low and the by-product Difficult to separate, so the author did not do further research

[0004] In summary, although the research on the aziridine cycloaddition reaction has made some progress, there are relatively few reports on the cycloaddition reaction of related aldoximes and aziridine compounds; therefore, looking for greener reaction conditions In particular, the reaction conditions of simpler and cheaper catalysts are used to complete the ring-forming reaction of aldoxime and aziridine, so that the reaction is easier to operate, more environmentally friendly, and the product yield and regioselectivity are higher. It is worth further exploration and discover

Images