Study On The Synthesis Of Spiroheterocyclic Compound By Azomethine Ylide

Due to the special structure of the spiro-compound molecules, computersimulations show that the molecules containing this kind of structure often have avariety of drug activity, and compounds containing spiro structure are often theimportant source of drug precursor molecules. Dispite the synthetic methods of spirocompound are very much, the azomethine ylide way due to its high chemical selectivity,regioselectivity, simple reaction conditions and easy processing are widely used in thesynthesis of spiro compounds containing the hydroxyindole structure fragment,especially those demanding compounds for the stereoselective. In this paper, wesuccessfully used the azomethine ylides strategy, combined with the multi-componentreactions and ultrasonic technology to prepare a variety of spiroheterocyclic compounds.Three parts are included in this thesis：Part I: In this part, the synthesis of new spiroheterocyclic compounds withbarbituric acid and hydroxyindole structural fragments has been studied. The chalconescontaining barbituric acid structure were used as the dipolarophile to react with isatin/acenaphthene quinone, sarcosine/thioproline under conventional heating conditions,the target products have been obtained with high regional and stereoselectivity. Areasonable explanation for the regioselectivity of the product has been made, and theconfiguration of the products were determined by single crystal X-ray diffractionanalysis.Part II: In the second part, the four-component one-pot synthesis of spirocycliccompounds under ultrasonic radiation was described. The method does not requireadvance preparation of the dipolarophile, which provides a new way for ultrasonictechnology used in the synthesis of the spiroheterocyclic compound. Compared withconventional heating, the reaction time of this method is shorter and the yield is higher. Part III: The third part depicts the synthesis of spiro compounds containingoxazoline ketone structure through azomethine ylide. The chalcone with oxazolineketone moiety are taken as dipolarophile, isatin/acenaphthene quinone and sarcosine/thioproline are treated as the source of azomethine ylide. The reaction owning theadvantages of simple operation, convenient post-processing has high regioselectivityand stereoselectivity.