Ring Opening Reactions Of N-Tosylaziridines With Carboxyli Acids In Dimethyl Formamide

N-Tosylaziridines is the important intermediates in organic synthesis and having physical active structure unit compounds,which have been widely used in the synthesis of natural products and medical reagents.Because ternary heterocyclic has a greater tension,It's easy to open the ring,reacted with different nucleophiles.Through reaction with all kinds of other nucleophilic which containing carbon?nitrogen?oxygen?sulfur and halogen element can be synthetized amino acids?diamine?chiral ligands and other bioactive compounds.So,Aziridines have recently received attention as versatile intermediates and important precursors for the synthesis of many nitrogen biologically interesting molecules.Part one present application of TBAB(Tetrabutylammonium Bromide)as an efficient catalyst for the ring opening of aziridines with Carboxylic acids.Firstly,select N-tosylcyclohexylaziridine with 4-nitrobenzoic acid as the model reaction to optimize the React Conditions,obtain the best reaction conditions:10 mol%TBAB as the catalyst,reaction temperature 65 ?,DMF 2.0 mL as solvent,1.2 equiv of 4-nitrobenzoic acid.After the optimization of the condition,the yield of product is ninety-six percent.A variety of aromatic and aliphatic N-tosyl aziridines and carboxylic acid were extended and corresponding products were obtained in moderate to good yields.After extend the substrate,twenty-three new products were obtained,all of these products were examined by 1HNMR?13C NMR?HRMS.Part two selected the Dimethyl Formamide as the solvent,didn't add TBAB,N-tosylcyclohexylaziridine with 4-nitrobenzoic acid as the model reaction to optimize the new Reaction Conditions,obtain the best reaction conditions:reaction temperature 65 ?,DMF 2.0 mL as solvent,1.2 equiv of 4-nitrobenzoic acid,then extend the substrate,found if lacking TBAB,most substrates had a lower yields,also had a longer reaction time.This research found that by TBAB as catalyst can effectively promote the reaction of nitrogen heterocyclic with carboxylic acid,The advantages of this method:(1)using less TBAB,saving much costs;(2)higher yields of products,has some significance to practice use;(3)mild reaction condition,simple experimental aftertreatment,easy obtaining products;(4)good regioselectivities.