Research On The Reaction Of Organozinc Reagents With N-sulfonylimines Under The CuI-catalyzed

Sulfonamide is a hot topic in the research of the drug in recent years for its extensive biological activity in medicine and pesticide. In this paper, we made a detailed overview on sulfonamide compounds in recent researches and studied the synthesis of sulfonamide compounds, developed and optimized a new method of synthesis on sulfonamide compounds.In this thesis, two aspects of the application and synthesis of the sulfonamide compounds were made a detailed summary in recent years. The direct addition of organometallic reagents to imines is a very convergent route to α-branched primary and secondary amines. Consequently, a number of synthetically useful addition reactions for the formation of carbon–carbon bonds have been developed with organolithium, Grignard, dialkyl zinc, alkenyl zirconium, aryl tin, aryl titanium, and aryl boron reagents as nucleophiles. Despite this great progress, limitations in the scope of this reaction remain, especially with regard to functional-group compatibility. Highly reactive organometallic species, such as organolithium or Grignard reagents, have typically been used for the alkylation of imines, as the reactions occur under mild conditions with such reagents. However, drawbacks associated with these organometallic reagents are the competitive formation of reduction products and difficulties in the reconciliation of reactivity and chemoselectivity when functional groups are present in either the nucleophile or the imine substrate. The use of softer boron, tin, or silicon reagents has been limited mainly to arylation reactions and resonance-stabilized allyl metal species, which are more reactive than ordinary alkyl organometallic reagents. Organozinc reagents show an optimal compromise in terms of reactivity and wide functional-group tolerance, but only a limited number of simple dialkyl zinc reagents(typically dimethylzinc or diethylzinc) have been used for the alkylation of imines. Owing to their straightforward preparation and commercial availability, alkyl zinc halides offer a unique opportunity to satisfy the need for a general method for the alkylation of imines that combines high reactivity and wide functional-group tolerance. Although an increasing number of methodologies benefit from the unique reactivity/selectivity profile of RZnX reagents, alkyl zinc halides have been scarcely used as nucleophiles in 1,2-addition reactions to imines, probably as a result of the poor electrophilicity of the imine group. We have explored the application of organozinc reagents in the synthesis for a long time, based on this, we hope the direct addition of organozinc reagents to N-atom of the imine which has electron-withdrawing group can occur on the presence of the suitable catalyst and ligand.In this thesis, a series of N-sulfonylimines were prepared, on the basis of the above works, research on the reaction of organozinc reagents with N-sulfonylimines under the Cu I-catalyzed were studied. To our knowledge, this addition reaction has never been reported. We have examined the effect of solvent polarity, temperature and time on the reaction and changed reaction scale, which were taken for the optimization system. Good results were observed, more than 30 functionalized sulfonamide compounds were synthesized, and their structures had been determined by IR, 1HNMR and 13 CNMR. A new way of the synthesis of these compounds was provided...