Study On The Synthetic Method Ofα,β-unsaturatedAcyl-substituted Oxazolidone And Imido Derivatives

The β-diketone of α,β-unsaturated acyl-substituted oxazolidone and imidoderivatives can be formed into compexes with chiral metal catalyst followed ingood stereoselectivity. And thus it is widely used in the asymmetric studies ofalkylation, acylation, Diels-Alder reaction and1,3-dipolarcycloaddition reactions.At the present, the synthetic routes of these compounds were complex and harsh.So in this paper we focused on the synthesis of α,β-unsaturated acyl-substitutedoxazolidone and imido derivatives in the improved methods. Then we studied the1,3-dipolarcycloaddition reactions of N-acryloylisoindoline-1,3-dione and(Z)-N-benzylideneaniline oxide in addition reaction.This paper has studied on the synthetic methods of acyloyl-oxazolidinoneand acyloyl-pyrrolidinedione derivatives by using simple raw materials. Specificcontent is as follows:Synthesis of α,β-unsaturated cinnamic acid derivatives: we used six kinds ofaromatic aldehydes as raw materials, malonic acid as reagent, pyridine as solventto synthesize target compounds by Knoevenagel reaction. All the yields wereover90.0%.Synthesis of succinimide, phthalimide and2-oxazolidone: we used succinicacid and ammonia to synthesize succinimide (yield:81.0%), O-phthalicanhydride and ammonia to synthesize phthalimide (yield:76.8%), amino-ethanoland carbamide to synthesize2-oxazolidone (yield:72.1%).Synthesis of α,β-unsaturated acyl-substituted oxazolidone and imidoderivatives: first, we reacted α,β-unsaturated carboxylic acid with SOCl2to get α,β-unsaturated chloride. And then reacted with2-oxazolidone, succinimide,phthalimide to synthesize the α,β-unsaturated acyl-substituted oxazolidone andimido derivatives respectively. All the yields were over90.0%.The application of the1,3dipolar cycloaddition: we completed the modelreaction of (Z)-N-benzylideneaniline oxide and N-acryloylisoindoline-1,3-dione,the result showed that we could mainly get4-substituted product in the roomtemperature. But when we added Lewisacid as catalyst, the product was finallychanged into3-hydroxy-1,5-diphenylpyrrolidin-2-one. In this paper, we gavedetailed characterization to the structure of byproduct and predicted themechanism in order to settle the new research foundation for the1,3-dipolarcycloaddition.