A Novel Synthesis of N-sulfonylformamidines From (Diarene and Dialkyl)sulfonimides

Abstract

Compounds containing the N-sulfonylformamidine moiety have antiproliferative, antiresorptive and antitumor activity. In particular, these compounds act as efficient inhibitors of gastric acid incretion. Several synthetic methods of N-sulfonylformamidine from N-sulfonamide or azide have already been reported. However, these methods require high temperatures and hazardous reagents. Here, we investigated the synthesis of Nsulfonylformamidine from (diarene and dialkyl)sulfonimide under mild conditions for the first time. Experiments were done at room temperature under aerobic conditions, and the desired products were obtained at excellent yields.The variation in the substituents have an important role in the reactions. In the case of the electron-donating group, the desired products were obtained at a 60-97% yield. On the other hand, (diarene and dialkyl)sulfonimides which include an electron-withdrawing group, remained as starting materials after a long time; therefore, the reactions were done under different conditions, which included higher temperatures or greater amounts of 4-toluenesulfonyl chloride (TsCl). As a result, we obtained a 61-100% yield. Moreover, (diarene and dialkyl)sulfonimides, which include the aliphatic moiety, yielded the desired product with a 77-100% yield. Furthermore, reactions with various substituted formamides yielded the product at a 66-97% yield.