Studies On The Synthesis Of Fused Heterocyclic Derivatives From Arnes

This thesis mainly focused on the synthesis of naphthoxindoles or phenanthrofuranones by[4+2]cycloaddition reactions of 3-methyleneindolin-2-ones or 3-methylenebenzofuran-2-one with benzyne generated in situ from benzobis?oxadisilole?.The synthesis of anthraoxindoles by[4+2]cycloaddition reactions of 3-methyleneindolin-2-ones with naphthyne generated in situ from2,3-naphthoxadisilole.Studies on the synthesis of 5H-dibenzo[b,g]thiocin-5-ones or5H-benzo[b]naphtho[2,3-g]thiocin-5-one derivatives by[3+2]cycloaddition reactions and?-elimination reactions of 2-methylenebenzothiophene-3-ones with arynes generated in situ from benzobis?oxadisilole?,2-?trimethylsilyl?phenyl trifluoromethanesulfonate or 2,3-naphthoxadisilole.The first part:Studied on the synthesis of naphthoxindoles or phenanthrofuranones by[4+2]cycloadditionreactionsof3-methyleneindolin-2-onesor3-methylenebenzofuran-2-one with benzyne generated in situ from benzobis?oxadisilole?.The synthesis of anthraoxindoles by[4+2]cycloaddition reactions of 3-methyleneindolin-2-ones with naphyne generated in situ from2,3-naphthoxadisilole.The photophysical,redox and thermal properties of naphthoxindoles and anthraoxindoles were characterized.The simplicity of these procedures and atomic economy should offer convenient way for the synthesis of heterocyclic compounds.The second part:Studied on the synthesis of the 5H-dibenzo[b,g]thiocin-5-ones or5H-benzo[b]naphtho[2,3-g]thiocin-5-one derivatives by[3+2]cycloaddition reactions and?-elimination reactions of 2-methylenebenzothiophene-3-ones with arynes generated in situ from benzobis?oxadisilole?,2-?trimethylsilyl?phenyl trifluoromethanesulfonate or 2,3-naphthoxadisilole.One-step synthesis of8-membered sulfur heterocyclic compounds by the reaction of arynes with2-methylenebenzothiophene-3-one derivatives has many advantages,such as innovative synthesis method,high yield,mild reaction conditions,simple operation,rapid reaction and good applicability.The effective synthetic routes of dibenzo[b,g]thiocin-5-one and benzo[b]naphtho[2,3-g]thiocin-5-one derivatives are well provided,and the synthetic methods of organic sulfur-containing octacyclic compounds are enriched.The structures of these new compounds were confirmed by ¹H NMR,¹³C NMR,IR,LRMS,HRMS and X-ray spectroscopy.