The Cycloaddition Reactions Of N-Tosylaziridines With Oximes

Aziridines are a kind of versatile intermediates in organic synthesis, which have a three-membered ring structure. They can react with different types of nucleophiles to afford various amino compounds. The compounds have attracted many chemists’and pharmacologists’attention due to their unique structure which have a wide range of application in drug synthesis. The ring-opening reactions of aziridines with nucleophiles has not uncommon, but the study of related reaction of aziridines continues attracting people’interest. Among of these reactions, the cycloaddition reactions of aziridines have drawn increasing interest. More and more cycloaddition reactions of aziridines with dipolarophiles such as alkenes, alkynes, have been reported. About reports of cycloaddition reactions of aziridines with oximes are relatively rare, which greatly aroused our interest.This paper proposes a KOH as catalyst in acetonitrile solvent to achieve the cycloaddition reaction of aziridines with oxime. In this reaction:select N-tosylcyclohexylaziridine with benzaldehyde oxime as the model reaction to optimize the react conditions, obtain the best reaction conditions 10 mol% KOH as the catalyst, CH3CN 0.5 mL as solvent, reaction temperature 70℃, reaction substrate material ratio of 1:1.2. The total yield of the product reached 96% under optimum conditions. A variety of aromatic and aliphatic N-tosylaziridines and oximes were extended and corresponding products were obtained in moderate to good yields. After extend the substrate, many new products were obtained, all of these products were examined by 1HNMR、13C NMR、HRMS.We find that the KOH as catalyst can effectively promote the cycloaddition reaction of aziridines with oxime, the reaction has the following advantages:(1) Simple reaction system and the experimental operation, mild reaction conditions; (2) The product is the basic skeletal structure of many drug molecules, provides a new method for drug synthesis. Therefore, the reaction has a certain practical value as the new heterocyclic cycloaddition reaction.