N-未保护及N-保护炔基磺酰胺的合成

lkynylsulfonamides and their derivitives are a class of organic molecules featuring both alkynyl and sulfonamidyl groups. Their unique chemical architecture endows them with versatile reactivity, making them prevalent in biologically active molecules. In light of the current scarcity of reports on the synthesis and chemical properties of alkynylsulfonamide compounds, this study employs a "one-pot" synthesis strategy involving the dual nucleophilic substitution reaction of alkynes, sulfuryl chloride, and aliphatic amines, producing alkynylsulfonamides in satified yields. The substrate scope was explored. The resulted sulfonamides were further protected by using acyl chlorides and sulfonyl chlorides. Experimental results demonstrated that both electron-withdrawing and electron-donating aryl alkynes, as well as alkyl alkynes, could participate in the dual nucleophilic substitution, affording the corresponding alkynylsulfonamides. The reaction between alkynylsulfonamides and acyl chlorides was achieved in the presence of 4-dimethylaminopyridine (DMAP) and triethylamine, while the reaction with sulfonyl chlorides was facilitated by strong bases such as n-butyllithium. This work provides a concise access to both N-free and N-protected alkynylsulfonamides.