Study On The Catalytic Reaction Of Propargyl-N,O-hemiacetal With Amine And Diphenylphosphine, Respectively

Propargylamines are a kind of important organic synthetic intermediates,which can be widely applied to the synthesis of bioactive nitrogen-containing compounds,natural products and drug molecules.Diphenylphosphine oxide as a cheap and stabilized phosphinylation reagent,has wide application in the field of organic synthesis.In the first part of this article,we summarized traditional synthesis methods of propargylamines and their research development in asymmetric catalytic synthesis area,some research progress of organic phosphorus compounds were introduced either.In the second part of this article,we introduced the project design,research methods and research results of this paper.At the beginning of experiment part,reactions between popargyl-N,O-hemiacetal and amines were studied.We found that the primary amine can react with propargyl-N,O-hemiacetal reaction and produced an acetylene imine compound,and two olefine aldehyde compounds were synthesized from reaction between propargyl-N,O-hemiacetal and secondary amines.Next,a lot of catalysts were tested in the research between propargylamines and diphenylphosphine oxide,the results have demonstrated that with benzoic acid and triethylamine as catalyst respectively,propargylamines phosphonic compounds and alkenyl phosphorus compounds were synthesized as main products respectively.The optimized reaction conditions are toluene as solvent,0.1 equivalent catalyst and 10 hours reaction time under the 80? temperature.And the scopes of reaction were extended,10 A type phosphonic propargyl amine compounds and 6 B type alkenyl phosphorus compounds were obtained.