Synthesis Of Sulfonyl Substituted Pyran Compounds And Arylsulfonamides Based On Multi-component One-pot Method

Pyran derivatives are an important class of oxygen-containing heterocyclic compounds among organic compounds.Among the pyran derivatives,2-amino-4H-pyran compounds are a very important class of compounds.Such compounds have been widely found in the fields of medicine,pesticides and industry.In recent years,chemists have begun to develop various effective methods for synthesizing these compounds based on their ability to build the core structure of biologically active molecules or natural products.N-arylsulfonamide is a type of functional skeleton that is ubiquitous in a large number of pharmaceutically important molecules.Scientists early discovered that N-arylsulfonamides have anti-cancer,antibacterial,anticonvulsant and HIV protease inhibitory activities.Since then,N-arylsulfonamide derivatives have been widely used in SAR research for medicinal chemistry research.In summary,based on the wide range of biological and pharmacological activities of sulfonylpyrans and arylsulfonamides and the advantages of multi-component one-pot methods(MCRs),the synthesis of target compounds through multi-component one-pot methods has important research significance.The first chapter introduces the introduction of heterocyclic compounds,the latest research progress of green chemistry,the research progress and research overview of multi-component one-pot method(MCR).At the same time,the research progress and research overview of sulfonylpyrans and arylsulfonamides are introduced.Chapter 2 introduces the efficient synthesis of sulfonyl-substituted 2-amino-4H-through three-component one-pot reaction using ethanol as a green solvent,aromatic aldehyde,cyclic ketone and phenyl(or methyl)sulfonyl acetonitrile Pyran derivatives.This multi-component reaction is characterized by the use of inexpensive and non-toxic sodium L-ascorbate as a green catalyst,through a simple,effective and environmentally friendly way to obtain the target compound sulfonyl substituted 2-amino group in moderate to good yields 4H-pyran derivatives.Finally,the obtained target compound was structurally characterized by ¹H NMR,¹³C NMR,IR,etc.,to further determine the final product structure.We have also proposed a reasonable reaction mechanism for the green synthesis of sulfonyl-substituted 2-amino-4H-pyrans using sodium L-ascorbate as a catalyst.Chapter 3 introduces the three-component one-pot synthesis of arylsulfonamide derivatives by aromatic amine,DABSO and tert-butyl hydroperoxide(TBHP)using DMSO as solvent and I₂ as catalyst.Through the above synthesis methods,we have obtained six arylsulfonamide derivatives in total,and all substrates can obtain the target compounds in moderate to good yields.Finally,all the above target compounds were structurally characterized by ¹H NMR,¹³C NMR,HRMS,IR,etc.,to further determine the final product structure.