Synthesis Of Sulfonamide Compounds Based On Sulfonylhydrazide And Triethylamine

The arylsulfonyl radical addition reaction is a kind of reaction with high atom utilization rate,and is a very effective method for constructing C-N bond and C-SO₂bond.To this end,the C-SO₂ radical coupling addition reaction is a very effective way to construct molecular skeletons of various drug intermediates.The benzenesulfonamides have biological activity and play an important role in anticancer,antitumor and antidiabetic clinical applications and are often used as antiviral and antibacterial agents in the field of pesticides.However,benzenesulfonyl enamines are also biologically active like sulfonamides and have a wide range of applications in organic synthetic chemistry,so the development of such compounds is of great significance.In recent years,the free-radical coupling addition reaction of arylsulfonylamines has been reported in some literatures,mainly through the non-metal catalysis,the synthesis of such compounds,but the use of benzenesulfonyl hydrazide as a sulfonyl source of metal catalytic freedom The base reaction has hardly been reported.In view of the above research reports,the authors reported a method for the free radical addition of benzenesulfonylhydrazide using copper salts and peroxides.The specific contents are as follows:1.This paper introduces the synthesis of benzenesulfonyl hydrazide.A series of arylsulfonyl hydrazide is used as a raw material to form a nucleophilic substitution reaction with hydrazine hydrate.A series of different substituents of benzenesulfonyl hydrazide are synthesized.2.Using p-methylbenzenesulfonylhydrazide and triethylamine as template,the reaction conditions were screened,and the conditions of solvent,catalyst,catalyst equivalent,oxidant,oxidant equivalent,reaction temperature and time were investigated.,the best reaction conditions were obtained.The applicability of the benzenesulfonyl hydrazide with a different substituent on the phenyl ring and the heterocyclic sulfonyl hydrazide was investigated.Under the optimal conditions,21target compounds were synthesized,and their structures were confirmed by NMR,IR,MS and HRMS.Based on the previous literature reports,combined with the experience of the laboratory brothers and sisters,the author proposed a possible reaction mechanism,through the control experiment,to make a reasonable verification of the possible mechanism of the reaction.The most important characteristics of the reaction are good atom economy,mild reaction conditions and simple operation.At the same time,it has good applicability to different substrates under the optimal reaction conditions,and has good applicability to common substituents.