N-苯磺酰咔啉的合成

Synthesis of N-benzenesulfonylcarboline

描述了碱性条件下咔啉类化合物的苯磺酰胺化反应。在Na H作用下,具有两亲结构的β-或γ-咔啉与N-氟代双苯磺酰胺反应生成不同种类的目标化合物,实现咔啉苯磺酰胺的简便合成,收率良好。机理研究表明,在反应中间体咔啉氮负离子的影响下,N-氟代双苯磺酰胺的N—S键断裂提供苯磺酰基,这是商品化试剂N-氟代双苯磺酰胺作为亲电氟化、自由基氟化和胺化试剂之后新的应用。

A convenient synthesis of carboline sulfonamide was achieved via sulfonamidation under alkaline conditions.The reactions between β-or γ-carbolines and N-fluorobenzenesulfonamide were investigated in the presence of Na H.With N-fluorobenzenesulfonamide as sulfonylation reagent,β-and γ-carboline benzene sulfonamide derivatives were obtained in good yields.These reactions provide a new pathway for carboline sulfonamide derivatives.The mechanism study showed that under the influence of the reaction intermediate carboline nitrogen anion,the N—S bond cleavage of N-fluorobisbenzenesulfonamide provided abenzenesulfonyl group,which was the commercial reagent N-fluorobisbenzenesulfonamide as a new application after electrofluorination,free radical fluorination and amination reagents.