The Research In The Ring Opening Of Aziridine With Carboxylic Acids Using KOH As Catalyst

Aziridines are widely recognized as a significant and versatile building blocks for the synthesis of various biologically active compounds.Their activity has led to wide research and use in the ring-opening reactions with a range of nucleophiles.As a result,this area has attracted a great deal of attention.Although there has been a great deal of interest in the ring opening of N-tosylaziridines with various nucleophiles,comparably few examples on the ring opening with carboxylic acids and their derivatives are observed.A novel application of DMSO as solvent,and KOH as a base reagent for the ring opening of aziridines with carboxylic acid.The reaction conditions were optimized by the solvent type,catalyst type,catalyst Loading,solvent dosage,tempreture,and carboxylic acid equive.The optimal reaction conditions:cyclohexane N-tosylaziridines 0.2 mmol as standard substrate,carboxylic acid 1.2 equ.,KOH 40 mol%as the base reagent,reaction temperature 45?,DMSO 1 mL as solvent.A total of 14 kinds of N-tosylaziridines and 12 kinds of carboxylic acid were extended,and corresponding product obtained good yields but a common regioselectivity.1HNMR,13CNMR and HRMS were used to identify the products,and determine the isomer ratio of reaction product.The advantages of this method include:(1)DMSO is a environmentally friendly solvent;(2)simple experimental operation,mild reaction conditionand and short reaction time;(3)most reaction has very good yield.Therefore,this research has a great usefulness in synthetic chemistry.