The Cycloaddition Reactions Of N-tosylaziridines With Nitrosocompounds

Aziridines are a kind of versatile intermediates in organic synthesis.They can undergo cycloadditions with many reagents to afford various cyclic compounds.These compounds have attracted many chemists’and pharmacologists’attention because they have wide applications in drug synthesis.Although the cycloadditions about aziridines have had many reports,the increasing interest is focused on.More and more cycloadditions of aziridines with dipolarophiles such as alkenes,alkynes,have been realized.However,the cycloaddition of aziridines with nitrosocompounds are relatively rare,which greatly aroused our interest.The cycloadditions of aziridines with nitrosocompounds using Ni（ClO₄）₂·6H₂O as a catalyst or ZnCl₂ as a promoter were realized.The reaction of N-tosylcyclohexylaziridine with nitrosobenzene was selected as the model reaction to optimize reaction conditions.Ni（ClO₄）₂·6H₂O provided the products in up to 95%yield and ZnCl₂ afforded the products with up to 88%yield under optimal conditions.Subsequently,a variety of N-tosylaziridines and nitrosocompounds were extended and the corresponding products were obtained in moderate to good yields.Many new products were afforded during the course and they were determined by ¹HNMR、¹³C NMR and HRMS.It was found that Ni（ClO₄）₂·6H₂O as a catalyst or ZnCl₂ as a promoter could effectively promote cycloadditions of aziridines with nitrosocompounds,respectively.The reaction has the following advantages:（1）Simple reaction system and mild reaction conditions;（2）The reaction provides a new method for synthesis of drug intermediates.Therefore,the reaction has certain practical value.