Domino Reaction Of Thioaurone Analogues With Arynes Precursor Or Sulfur Ylides

Sulfur-heterocycle compounds have a wide range of applications in medicinal chemistry and materials chemistry,so it is significant to develop new synthetic methods to synthetize sulfur-heterocycle compounds.This thesis mainly studies the reaction of thioaurone analogues with arynes precursor or sulfur ylides,respectively.Development of new domino reactions based on the advantages of the conjugated double bond of thioaurone and the sulfur atom can be stabilizing the adjacent carbon anion.And then synthesis of a series of new compounds.The main work has the following two aspects:(1)As aryne precursors can be prepared under mild conditions,this highly active compound has aroused great interest of chemists in recent years.Firstly,the reaction of thioaurone analogues with Kobayashi aryne precursor has been studied.Through the[3+2]cycloaddition reaction,1,2-hydrogen transfer,and C(Sp2)-S bond cleavage,when the thioaurone has an electron-donating group,the construction of eight-membered cyclic diaryl sulfides can be efficiently prepared.when thioaurone has halogen-substituented,a[5,5]diaryl sulfides analogues is formed.The mechanism of the reaction was studied by DFT,and the different C-S bond cleavage under different types of substituent were initially discussed,to synthesize the above two sulfur-heterocyclic compounds.The reaction conditions are mild,and a series of eight-membered cyclic diaryl sulfides,which is difficult to synthesize by other methods to provide the possibility for the eight-membered cyclic diaryl sulfides in the process of high-throughput screen of drug molecules.(2)Crotonate-derived sulfur ylides have received recent attention due to their versatile reaction modes.This thesis studies the domino reactions between thioaurones or their analogues and crotonate-derived sulfur ylides,and efficiently synthesize a series of 3-benzothiophene-substituted chromene.in this reaction,It is more significant that crotonate-derived sulfur ylides act as two-carbon synthon(?and?carbons),which was very rare in previous reports.A total of 40 new compounds were synthesized in this thesis.All the compounds were characterized by ¹H NMR,¹³C NMR,IR,HRMS,m.p.and the structure of representative compounds was confirmed by X-ray crystal.