Synthesis Of Quinazolinones And Amino-(N-alkyl)-Benzenesulfonamides Derivatives Catalyzed By Heterogeneous Iridium Catalyst

Quinazolinones and amino-(N-alkyl)benzenesulfonamide compounds are important nitrogen-containing compounds.Quinazolinone derivatives are the core structures for constructing biologically active molecules and drug molecules,which exhibit a wide range of biological and pharmacological effects;amino-(N-alkyl)benzenesulfonamides are important structural motifs in many natural products and other biologically active molecules and were also utilized as key synthetic intermediates.Compared with traditional synthesis methods,many efficient and green synthesis methods have been developed.However,these synthesis methods have some shortcomings,such as low catalyst recovery rate and large activity loss,which may cause heavy metal ion pollution and high cost,reduction of overall yield caused by stepwise reaction,etc.Polyvinylpyridine(PVP)and covalent triazine skeleton(CTF)are two different types of polymers with good thermal and chemical stability,and they are good carriers for the preparation of heterogeneous catalysts.In this thesis,based on the mechanism of "acceptorless dehydrogenation" and "hydrogen autotransfer",two transition metal heterogeneous catalysts were prepared using PVP and CTF materials,which were used for quinazolinones and amino-(N-alkyl)benzenesulfonamides compounds.The preparation has the advantages of high atomic efficiency and environmental friendliness.It not only retains the advantages of high activity and high selectivity of the homogeneous catalyst,but also has the advantages of heterogeneous catalytic systems such as easy separation from the product and easy recycling.Corresponding characterization and catalytic performance research were carried out,and the related catalytic reaction mechanism was studied.The iridium-loaded poly-(4-vinylpyridine)Cp*Ir@P4VP catalyzed o-aminobenzonitrile and aldehyde to prepare quinazolinone derivatives via selective hydration/acceptorless dehydrogenative coupling.The reaction showed high catalytic activity.After 5 cycles of the catalyst,there is no significant loss of activity.The covalent triazine skeleton Cp*Ir@CTF loaded with metal iridium was used to prepare amino-(N-alkyl)benzenesulfonamide derivatives.Cp*Ir@CTF has better recycling properties.It is worth noting that this study shows the potential for the recognition of different amino groups in the N-alkylation reaction of complex molecules.In addition to the formation of the corresponding quinazolinone and amino-(N-alkyl)benzenesulfonamide derivatives in these two reactions,the by-products are only water and hydrogen,which meets the requirements of green chemistry.